Personal Account

THE CHEMICAL RECORD

Carbon Dioxide Incorporation into Alkyne Compounds Mediated by Silver Catalysts Satoshi Kikuchi and Tohru Yamada*[a] Department of Chemistry Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan) E-mail: [email protected]

[a]

Received: September 9, 2013 Published online: January 13, 2014

ABSTRACT: We have reported that a silver catalyst with a base was an effective system for the incorporation and utilization of carbon dioxide in organic syntheses under mild reaction conditions. The C≡C triple bond activation by the silver catalysts was assumed to be a key step in these reactions, which was supported by DFT calculations with a model substrate. Based on these reports, we recently developed three new CO2 incorporations under the mild reaction conditions using our silver catalyst system. In this Personal Account, we describe the silver-catalyzed CO2 incorporation with C–C bond formation to afford the corresponding γ-lactone derivatives and the synthesis of benzoxazin-2-one derivatives and 4-hydroxyquinolin-2(1H)-one derivatives from alkynylanilines with carbon dioxide catalyzed by silver salts. DOI 10.1002/tcr.201300025 Keywords: carbon dioxide fixation, heterocycles, homogeneous catalysis, silver, synthetic methods

1. Introduction Since the onset of the Industrial Revolution, enormous amounts of carbon dioxide have been emitted into the atmosphere from the oxidation of hydrocarbon fuels to support the energy demands of our modern comfortable and convenient lifestyles.[1] Much effort has been made towards the development of an efficient incorporation and utilization of carbon dioxide as well as to the regulation of carbon dioxide. Various chemical reactions have been reported to produce useful bulk chemicals from carbon dioxide, e.g., the manufacture of salicylic acid using the Kolbe–Schmitt process or the production of polycarbonate and urea. Carbon dioxide is also an attractive C1 feedstock for organic synthesis due to its ubiquity, abundance, and reduced toxicity compared to the alternative feedstocks; however, because of its lower reactivity, harsh reaction conditions are required to activate and incorporate carbon dioxide into

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organic compounds.[2] It is necessary to develop a mild reaction system including catalysts to efficiently capture carbon dioxide and convert it into a wide variety of substrates, especially fine chemicals. Recently, we reported that a catalytic amount of a silver salt as a π-Lewis acid to activate an alkyne, combined with DBU, was an efficient catalyst system for the reaction of carbon dioxide with propargylic alcohols[3a] and propargylic amines[3b] to produce the corresponding cyclic carbonates and oxazolidinones,[4] respectively, in good to excellent yields (Scheme 1). We have also reported that the Meyer–Schuster-type rearrangement was mediated by carbon dioxide in the presence of a catalytic amount of silver methanesulfonate and a base in polar solvents to afford the corresponding enones in high yields.[5] Based on mechanistic studies using labeled C18O2 and

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© 2014 The Chemical Society of Japan and Wiley-VCH, Weinheim

Silver-Catalyzed Carbon Dioxide Incorporation into Alkynes

Scheme 2. Asymmetric incorporation of carbon dioxide.

Scheme 1. The reaction of carbon dioxide with propargyl alcohols and propargyl amines.

GC-MS, it was suggested that the reaction proceeded via an allene intermediate with an intramolecular [3,3]-sigmatropic rearrangement of the carbonate intermediate. Theoretical analysis of the silver catalytic system with N-methyltetrahydropyrimidine as a model base revealed that the transition state would provide the (Z)-exo-alkene product and that the solvent polarity would influence the reaction course for the cyclic carbonate or α,β-unsaturated carbonyl compound.[6] Consequently, it was confirmed that the activation of the C≡C triple bond by the silver catalyst as a π-Lewis acid was essential for these reactions. We also reported that an optically active Schiff base ligand for the silver catalyst achieved desymmetrization of symmetrical bispropargylic alcohols into the corresponding cyclic carbonates in good to excellent yields with a high enantioselectivity (Scheme 2).[7]

Tohru Yamada was born in Hokkaido, Japan, in 1958. He received his Ph.D. degree in 1987 from the University of Tokyo under the guidance of Professor Teruaki Mukaiyama. In 1987 he joined Mitsui Petrochemical Ind. Ltd. In 1997, he moved to Keio University to become an Associate Professor in the Chemistry Department, and in 2002 was promoted to Full Professor, and then in 2012 to Department Chair. He was a recipient of the Chemical Society of Japan Award for Young Chemists in 1992. His articles were awarded a BCSJ Award by the Chemical Society of Japan in 2003 and 2011. He was awarded the Society of Synthetic Organic Chemistry, Japan Nissan Chemical Industries Award for Novel Reactions & Methods in 2010.

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Based on our previous reports, when a substrate containing a nucleophilic part and a C≡C triple bond in the appropriate position is subjected to the present catalytic system under a CO2 atmosphere, the corresponding CO2incorporated product is obtained. In this Personal Account, we describe the silver-catalyzed CO2 incorporation with C–C bond formation under mild conditions to afford the corresponding γ-lactone derivatives[8] and the synthesis of benzoxazin-2-one derivatives[9] and 4-hydroxyquinolin-2(1H)-one derivatives[10] from alkynylaniline derivatives using carbon dioxide.

2. CO2 Incorporation with C–C Bond Formation The reaction of enolates with carbon dioxide has been reported to produce the corresponding β-ketocarboxylic acids. However, only limited types of substrates can be used, because βketocarboxylic acids are thermodynamically unstable and readily revert back to the starting substrate.[11] Therefore, we postulated that when a ketone containing an alkyne group at

Satoshi Kikuchi received his Ph.D. from the University of Tokyo in 2005 under the supervision of Professor Yukihiko Hashimoto. He became a Research Associate at Chuo University. In the middle of 2007, he became an Assistant Professor at Keio University, and was then promoted to a Junior Associate Professor in 2013. His current research interests include metal-catalyzed reactions and microwave chemistry.

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THE CHEMICAL RECORD

Scheme 3. The proposed reaction mechanism for C–C bond formation with carbon dioxide.

the appropriate position is applied to the present reaction system, the derived enolate would capture carbon dioxide to generate the corresponding β-ketocarboxylate, and the βketocarboxylate would then be trapped by the activated C≡C triple bond to afford the corresponding stable lactone (Scheme 3). We initially performed the reaction on the model substrate 1a in the presence of silver benzoate (20 mol%) with 2.0 equivalents of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) in DMSO under 1.0 MPa CO2 pressure, and found that the corresponding γ-lactone derivative 2a was obtained in 40% yield, with dihydrofuran derivatives formed as byproducts by the direct intermolecular cyclization of the enol derived from ketone 1a.[12] After optimization of the reaction conditions, it was found that MTBD (7-methyl-1,5,7-triazabicyclo [4.4.0]dec-5-ene) was an effective base and DMF was a suitable solvent for this reaction. The substrate scope of this reaction was then investigated (Table 1). The reactions of acetophenone derivatives having phenyl (1a), p-tolyl (1b), and p-trifluoromethylphenyl (1c) groups on the alkyne proceeded under the optimized reaction conditions to achieve high yields, irrespective of the electron-withdrawing or electron-donating nature of the group on the phenyl ring (Table 1, entries 1, 3, 4). When the catalyst loading was decreased from 20 mol% to 10 mol%, the reaction of ketone 1a with carbon dioxide produced the lactone 2a in good yield (entry 2), although a longer reaction time was required for the reaction to go to completion. The reaction of substrate 1d, having an n-butyl group, was also catalyzed in the presence of 6.0 equivalents of MTBD to afford the corresponding product 2d in good yields under 2.0 MPa CO2 pressure (entry 5). The p-tolyl ketone derivative 1e was a good substrate for this reaction and the corresponding product 2e was obtained in good yield (entry 6). The reaction of m-methoxyacetophenone derivative 1f proceeded in the presence of AgOBz (40 mol%) at

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10°C under 2.0 MPa CO2 pressure and the corresponding product 2f was obtained in good yields (entry 7). The 1-naphthyl derivative 1g was transformed into the corresponding lactone derivative 2g in 77% yield when 6.0 equivalents of MTBD were used (entry 8). The ketone 1h, having a cyclobutyl substituent, was also efficiently converted into the corresponding product 2h in good yield under the same catalytic system with 2.0 MPa CO2 pressure (entry 9). The present catalytic system was also applied to aliphatic ketone derivatives (1i, 1j, and 1k; Scheme 4) at 50°C under 2.0 MPa CO2 pressure. Substrate 1i was converted into the corresponding γ-lactone 2i in 58% yield. The yield of the γ-lactone 2j was not satisfactory (31%), but the reaction of ketone 1k with carbon dioxide afforded the corresponding γ-lactone 2k in 59% yield. These ketones possess two different protons, α and α′ to the carbonyl group, and thus two different enolates can be generated, but the γ-lactone was selectively obtained without the formation of any other lactone derivatives. The reaction to form the five-membered lactone is the productive pathway, and the corresponding γ-lactone was selectively obtained without any need for control of the enolization. The geometry of the C=C double bond in the lactone derivative 2e was confirmed by X-ray analysis to reveal the (Z)-isomer as the sole product (Figure 1). All other lactone derivatives were also selectively obtained as the (Z)-isomers based on NOE experiments.

3. The Reaction of Alkynylaniline and CO2 for the Synthesis of Benzoxazine-2-one Derivatives Benzoxazin-2-one derivatives have attracted much attention as some of the most important heterocyclic structures in pharmaceutical science; for example, the derivatives bearing an exo-olefin, 4-ylidene1,4-dihydro-2H-3,1-benzoxazin-2-ones, were reported to be active as osteoclast differential induction inhibitors or anti-inflammatory agents, as well as osteoclasis inhibitors and antirheumatic agents.[13] 4-Alkyl-substituted 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives also indicated biological behaviors with a modest progesterone receptor (PR) agonist activity, which have been used for contraceptives and hormone therapy, often in combination with estrogen.[14] Efavirenz (SustivaTM), composed of the benzoxazin-2-one system, was the first anti-HIV drug approved by the FDA in the United States.[15] In spite of the importance of the benzoxazin-2-one components, methods to reach them via organic synthesis have been limited. Several preparative reactions employing phosgene,[13,15–18] carbon monoxide,[19,20] carbonyldiimidazole,[14d] or a hypervalent iodine compound[21] have been reported for the synthesis of 4-alkylsubstituted benzoxazin-2-one derivatives. Synthetic reactions for benzoxazin-2-ones containing the exo-olefin have been only rarely reported, in which their scope was limited and toxic phosgene must be employed.[13,17]

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© 2014 The Chemical Society of Japan and Wiley-VCH, Weinheim

Silver-Catalyzed Carbon Dioxide Incorporation into Alkynes

Table 1. Application of the AgOBz and MTBD system in the reaction of several substrates.

Entry

Product

Time [h]

Yield[a] [%]

1 2[b] 3 4 5[c]

R1 = Ph (2a) C6H4p-Me (2b) C6H4p-CF3 (2c) n Bu (2d)

48 240 96 48 72

91 85 90 90 83

6 7[d,e] 8[c]

R2 = p-MeC6H4 (2e) m-MeOC6H4 (2f) 1-Naphthyl (2g)

72 144 120

84 77 77

9[f ]

(2h)

120

74

[a] Isolated yields. [b]AgOBz (10 mol%) was used. [c]The reaction was carried out with 6.0 equivalent of MTBD under 2.0 MPa CO2 pressure. [d]The reaction was performed at 10°C under 2.0 MPa CO2 pressure. [e]AgOBz (40 mol%) was used. [f ]The reaction was carried out under 2.0 MPa CO2 pressure.

Scheme 4. The reaction of aliphatic ketone derivatives.

We hypothesized that when o-alkynylaniline derivatives 3 are used as the starting substrates for the silver-catalyzed carbon dioxide incorporation reaction, the benzoxazin-2-one derivatives would be obtained via the 6-exo-dig cyclization on the activated C≡C triple bond (Scheme 5). At first, the reaction of the o-alkynylaniline derivative 3a with carbon dioxide was carried out in the presence of several metal salts, e.g., palladium, rhodium, platinum, copper, gold,

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Fig. 1. Single-crystal structure of 2e. Thermal ellipsoids are shown at 50% probability.

and silver salts, with DBU as a base. Among them, only the Ag salt was found to be an effective catalyst for this reaction to afford the corresponding benzoxazin-2-one 4a. The benzoxazepin-2-one derivative that might have been generated via the 7-endo-dig cyclization was not detected at

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4. The Efficient Synthesis of 4-Hydroxyquinolin2(1H)-one Derivatives from CO2

Scheme 5. The postulated reaction mechanism of o-alkynylaniline and carbon dioxide.

all. After optimization of the reaction conditions, various o-alkynylaniline derivatives were then subjected to the optimal reaction conditions (Table 2). The N-alkyl o-alkynylaniline derivatives could also be transformed into the corresponding products in excellent yields (Table 2, entries 2 and 3). The o-alkynylanilines with p-substitution 3d, 3e, and 3f were easily converted in high yields into the corresponding 6-substituted products 4d, 4e, and 4f, respectively (entries 4–6). The reactions of the substrates bearing the terminal alkyne 3g and internal alkyne 3h were smoothly performed to produce the corresponding products 4g and 4h in high yields (entries 7 and 8). The substrate having the 2-pyridyl group on the alkyne terminal position was also subjected to this catalytic system to afford the corresponding product 4i in excellent yield (entry 9). The geometry of the exo-olefin in the product 4b was confirmed by an X-ray diffraction analysis. This result revealed that the product was the benzoxazin-2-one containing the (Z)-exo-olefin as the sole compound. All other products were suggested to be the (Z)isomer based on NOE experiments. The present catalytic system was also successfully applied to various primary o-alkynylaniline derivatives with carbon dioxide (Scheme 6). The reaction of the o-alkynylaniline 3j, with a free amino group and a phenyl-substituted alkyne, was catalyzed by AgOAc in the presence of DABCO as a base to generate the benzoxazine derivative 4j in high yield. The substrate 3k, bearing the terminal alkyne, was also converted into the corresponding benzoxazine derivative 4k, but in an insufficient yield. The yield of 4k was improved to 75% when catalyzed by silver(II) picolinate instead of AgOAc. When the o-alkynylaniline derivative with a p-methyl group 3l was subjected to this catalytic system, the corresponding product 4l was obtained in 87% yield.

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During the study of the synthesis of the benzoxazin-2-one derivatives from CO2 with the activation of the C≡C triple bond by a silver catalyst, it was found that when DBU (1.0 eq.) was employed for the reaction of the primary o-alkynylanilines, the 4-hydroxyquinolin-2(1H)-one derivative was generated as the sole product instead of the benzoxazin-2-one derivative. Scheme 7 shows the hypothetical reaction mechanism to explain these observations. First, the corresponding benzoxazin-2-one would be formed from the o-alkynylaniline and carbon dioxide catalyzed by the silver catalyst. In the second step, the benzoxazine would immediately be deprotonated by the DBU base to generate the isocyanate and the enolate from C–O bond cleavage of the carbamate functionality. The enolate would then attack the carbon atom of the isocyanate to afford the 1,3-diketone intermediate, which would produce the corresponding 4-hydroxyquinolin-2(1H)one after enolization. Thus, in this proposed mechanism, a new C–C bond is formed with carbon dioxide. It is expected that the corresponding quinoline derivative should contain carbon dioxide. This hypothesis was supported by the mechanistic studies using labeled C18O2 and GC-MS and a time-resolved FT-IR analysis. The interest in 4-hydroxyquinolin-2(1H)-one derivatives has been growing due to their potential biological benefits. Studies on their medicinal properties have been promising, for example, in the treatment of central nervous system disorders,[22] sex hormone–related conditions,[23] and suppression of allergy-associated inflammations,[24] and some of their derivatives have been reported as HIV-1 inhibitors.[25] Their preparations have been based on conventional heterocyclic chemistry including nucleophilic addition-elimination reactions under harsh reaction conditions, such as the reaction of 4-halocarbostyril with potassium hydroxide,[26] or an aniline derivative and a carbonyl compound with high leaving group ability.[27] Although a few quinoline syntheses from o-alkynylaniline derivatives were known, the example of using CO2 as a reactant for the synthesis of quinoline derivatives had not been previously reported. Under the optimized reaction conditions, various oalkynylaniline derivatives were applied to the C–C bond forming, carbon dioxide incorporation reaction (Table 3). In the presence of 10 mol% AgNO3 and 1.0 equivalent of DBU under atmospheric pressure of carbon dioxide in DMSO, the aniline derivative 5a was transformed into the 4-hydroxyquinolin-2-one derivative 6a in excellent yield (entry 1). Anilines with substituents (R1) at the paraposition relative to the amino group were next subjected to the reaction. When o-alkynylaniline 5b substituted with an electrondonating group on the phenyl ring was employed, the corresponding product 6b was obtained in high yield (entry 2). The

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© 2014 The Chemical Society of Japan and Wiley-VCH, Weinheim

Silver-Catalyzed Carbon Dioxide Incorporation into Alkynes

Table 2. AgNO3 catalyzed the reaction of several o-alkynylaniline derivatives with carbon dioxide.

Product

Temp [°C]

Yield[a] [%]

1 2 3[b]

R1 = nPr (4a) Me (4b) i Bu (4c)

20 20 40

97 97 96

4 5 6

R2 = Me (4d) F (4e) CF3 (4f)

20 20 40

87 90 87

7[c] 8[c] 9

R3 = H (4g) n Bu (4h) 2-Py (4i)

60 40 20

80 86 99

Entry

[a]

Isolated yields. [b]The reaction was carried out for 35 h. [c]The reaction was carried out for 49 h.

AgOAc

Scheme 6. The silver-catalyzed reactions of several primary o-alkynylaniline derivatives with carbon dioxide.

4-hydroxyquinolin-2-one derivative 6c, with an electronwithdrawing group at the para-position, was also generated in high to excellent yields from 5c (entry 3). Substituents R2 on the alkyne terminal position were next examined. The substrate with a terminal alkyne 5d was transformed into a quinoline derivative 6d containing the trisubstituted olefin in 75% yield (entry 4). The substrate 5e, containing an alkyl substituent, was subjected to the

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Scheme 7. Hypothetical reaction mechanism for the formation of 4hydroxyquinolin-2-ones.

same conditions to afford the corresponding 3-alkyl-4hydroxyquinoline 6e in 69% yield (entry 5). Substrates with a 2-pyridyl group 5f, a 1-naphthyl group 5g, and a pmethoxyphenyl group 5h successfully afforded the corresponding products 6f, 6g, and 6h, respectively, in excellent yields (entries 6–8). The product having an enone structure 6i,

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THE CHEMICAL RECORD

Table 3. The synthesis of various 4-hydroxyquinolin-2(1H)-one derivatives.

5

Entry

6

Yield[a] [%]

Product

1 2 3

R1 = H (6a) CH3 (6b) F (6c)

97 82 98

4 5 6 7 8

R2 = H (6d) n Bu (6e) 2-Py (6f) 1-Naphthyl (6g) C6H4p-OMe (6h)

75 69 96 98 98

9 [a]

(6i)

pressure under mild reaction conditions. The key step in the reaction mechanism is proposed to be the generation of the isocyanate and the enolate through C–O bond cleavage and new C–C bond formation induced by deprotonation of the amide after formation of the benzoxazin-2-one. The obtained quinoline derivatives were composed of the starting oalkynylaniline and carbon dioxide, as revealed by isotopic labeling experiments. These reactions were catalyzed only by a silver salt. This advantage of the silver catalyst will be used for the incorporation and utilization of carbon dioxide to produce numerous important reactions in the near future.

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91

Isolated yields.

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5. Conclusions We have successfully developed the efficient CO2 incorporation and utilization catalyzed by silver salts in the presence of bases. Every reaction proceeded smoothly under mild reaction conditions to produce the corresponding products in good to high yields. A catalytic C–C bond forming reaction with carbon dioxide was employed with catalytic silver benzoate in the presence of MTBD to afford γ-lactone derivatives in good to high yields under mild reaction conditions. This reaction system could be applied to aliphatic ketone derivatives and the corresponding lactone was obtained without any control of the enolate formation. The silver catalyst in the presence of bases allowed the reaction of carbon dioxide with o-alkynylaniline derivatives to produce a series of benzoxazin-2-one derivatives in high yields under mild reaction conditions. Primary as well as secondary anilines could be used with this catalytic system to afford the corresponding products in good yields. We also developed a conceptually new synthetic method for 4hydroxyquinolin-2-one derivatives from o-alkynylanilines, DBU, a silver catalyst, and carbon dioxide at atmospheric

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Carbon dioxide incorporation into alkyne compounds mediated by silver catalysts.

We have reported that a silver catalyst with a base was an effective system for the incorporation and utilization of carbon dioxide in organic synthes...
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