Straightforward and Highly Efficient Synthesis of α-Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes

Chao Wu; Zhiwu Liang; Dong Yan; Weimin He; Jiannan Xiang

doi:10.1055/s-0033-1338513

Synthesis, Table of Contents

Synthesis 2013; 45(18): 2605-2611
DOI: 10.1055/s-0033-1338513

paper

Straightforward and Highly Efficient Synthesis of α-Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes

Chao Wu

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88821742 Email: wmhe@hnu.edu.cn Email: jnxiang@hnu.edu.cn

,

Zhiwu Liang

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88821742 Email: wmhe@hnu.edu.cn Email: jnxiang@hnu.edu.cn

,

Dong Yan

^bHunan Chemical Industry Vocation Technology Institute, Zhuzhou 412004, P. R. of China

,

Weimin He*

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88821742 Email: wmhe@hnu.edu.cn Email: jnxiang@hnu.edu.cn

,

Jiannan Xiang*

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88821742 Email: wmhe@hnu.edu.cn Email: jnxiang@hnu.edu.cn

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Abstract

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Abstract

A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O–H insertion.

Key words

alkynes - homogeneous catalysis - gold - oxidations - carbene complexes - ketones - esters

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References

References
1 Radüchel B. Synthesis 1980; 292

For esters as hydroxy functional groups, see:

2a Green TW, Wuts PG. M. Protective Groups in Organic Synthesis . Wiley; New York: 1991
2b Noyori R, Kitamura M In Modern Synthetic Methods . Vol. 5. Scheffold R. Springer; Berlin: 1989: 115

3 Chen Y, Chen C, Wu X. Chem. Soc. Rev. 2012; 41: 1742

4a Paulissen R, Reimlinger H, Hayez E, Hubert AJ, Teyssié P. Tetrahedron Lett. 1973; 14: 2233
4b Shinada T, Kawakami T, Sakai H, Takada I, Ohfune Y. Tetrahedron Lett. 1998; 39: 3757

5a Holshouser MH, Kolb M. J. Pharm. Sci. 1986; 75: 619
5b Rather JB, Reid EE. J. Am. Chem. Soc. 1919; 41: 75

6a Rubottom GM, Grube JM, Kincaid K. Synth. Commun. 1976; 6: 59
6b Demir AS, Camkerten N, Akgun H, Tanyeli C, Mahasneh AS, Watt DS. Synth. Commun. 1990; 20: 2279
6c Lee JC, Jin YS, Choi J.-H. Chem. Commun. 2001; 956

7 Mo D.-L, Dai L.-X, Hou X.-L. Tetrahedron Lett. 2009; 50: 5578

8a Zhang L, Sun J, Kozmin SA. Adv. Synth. Catal. 2006; 348: 2271
8b Hashmi AS. K. Chem. Rev. 2007; 107: 3180
8c Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
8d Huang H, Zhou Y, Liu H. Beilstein J. Org. Chem. 2011; 7: 897
8e Krause N, Winter C. Chem. Rev. 2011; 111: 1994
8f de Haro T, Nevado C. Synthesis 2011; 2530
8g Adcock HV, Davies PW. Synthesis 2012; 44: 3401
8h Lu B.-L, Dai L, Shi M. Chem. Soc. Rev. 2012; 41: 3318
8i Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448

9a Davies PW, Cremonesi A, Martin N. Chem. Commun. 2011; 47: 379
9b Lu B, Li C, Zhang L. J. Am. Chem. Soc. 2010; 132: 14070
9c Ye L, He W, Zhang L. J. Am. Chem. Soc. 2010; 132: 8550
9d Ye L, Cui L, Zhang G, Zhang L. J. Am. Chem. Soc. 2010; 132: 3258
9e He W, Li C, Zhang L. J. Am. Chem. Soc. 2011; 133: 8482
9f Qian D, Zhang J. Chem. Commun. 2011; 47: 11152
9g Chen D, Song G, Jia A, Li X. J. Org. Chem. 2011; 76: 8488
9h Ye L, He W, Zhang L. Angew. Chem. Int. Ed. 2011; 50: 3236
9i Noey EL, Luo Y, Zhang L, Houk KN. J. Am. Chem. Soc. 2011; 134: 1078
9j Bhunia S, Ghorpade S, Huple DB, Liu R.-S. Angew. Chem. Int. Ed. 2012; 51: 2939
9k Wang Y, Ji K, Lan S, Zhang L. Angew. Chem. Int. Ed. 2012; 51: 1915
9l Dateer RB, Pati K, Liu R.-S. Chem. Commun. 2012; 48: 7200
9m Xie J, Jiang H, Cheng Y, Zhu C. Chem. Commun. 2012; 48: 979
9n Chen D.-F, Han Z.-Y, He Y.-P, Yu J, Gong L.-Z. Angew. Chem. Int. Ed. 2012; 51: 12307
9o Gronnier C, Kramer S, Odabachian Y, Gagosz F. J. Am. Chem. Soc. 2011; 134: 828
9p Qian D, Zhang J. Chem. Commun. 2012; 48: 7082
9q Luo Y, Ji K, Li Y, Zhang L. J. Am. Chem. Soc. 2012; 134: 17412
9r Shu C, Liu M.-Q, Sun Y.-Z, Ye L.-W. Org. Lett. 2012; 14: 4958
9s Xu M, Ren T.-T, Li C.-Y. Org. Lett. 2012; 14: 4902
9t Fu J, Shang H, Wang Z, Chang L, Shao W, Yang Z, Tang Y. Angew. Chem. Int. Ed. 2013; 52: 4198

10a Li G, Zhang L. Angew. Chem. Int. Ed. 2007; 46: 5156
10b Shapiro ND, Toste FD. J. Am. Chem. Soc. 2007; 129: 4160
10c Davies PW, Albrecht SJ. C. Angew. Chem. Int. Ed. 2009; 48: 8372
10d Li C.-W, Pati K, Lin G.-Y, Sohel SM. A, Hung H.-H, Liu R.-S. Angew. Chem. Int. Ed. 2010; 49: 9891
10e Yeom H.-S, Shin S. Org. Biomol. Chem. 2013; 11: 1089

11a Yeom H.-S, Lee J.-E, Shin S. Angew. Chem. Int. Ed. 2008; 47: 7040
11b Yeom H.-S, Lee Y, Jeong J, So E, Hwang S, Lee J.-E, Lee SS, Shin S. Angew. Chem. Int. Ed. 2010; 49: 1611
11c Mukherjee A, Dateer RB, Chaudhuri R, Bhunia S, Karad SN, Liu R.-S. J. Am. Chem. Soc. 2011; 133: 15372

12 Xiao J, Li X. Angew. Chem. Int. Ed. 2011; 50: 7226
13 He W, Xie L, Xu Y, Xiang J, Zhang L. Org. Biomol. Chem. 2012; 10: 3168
14 Use of 1-ethynyl-2-methylbenzene as the substrate gave indan-1-one; see also ref. 9j. Use of 1-ethynyl-2-methoxy-benzene as the substrate gave 1-benzofuran-3(2H)-one; see also ref. 9t.
15 After submission of this manuscript, Zhang and co-workers reported the synthesis of carboxymethyl ketones from readily available carboxylic acids and terminal alkynes in the presence of a novel gold P,N-bidentate ligand catalyst, see: Ji K, Zhao Y, Zhang L. Angew. Chem. Int. Ed. 2013; 52: 6508
16 Zhou C, Zeng R, Zou J. Chin. J. Chem. 2010; 28: 294
17 Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
18 Kaila N, Janz K, Huang A, Moretto A, DeBernardo S, Bedard PW, Tam S, Clerin V, Keith JC, Tsao DH. H, Sushkova N, Shaw GD, Camphausen RT, Schaub RG, Wang Q. J. Med. Chem. 2007; 50: 40
19 Rubottom GM, Gruber JM. J. Org. Chem. 1978; 43: 1599

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