Rhodium-Catalyzed Aryl Migratory/Decarbonylation of Diaryl Ketones via the Activation of Unstrained C–C Bonds

Abstract

A Rh-catalyzed aryl migratory/decarbonylation of unstrained ketones has been developed. This viable transformation provides a complementary decarbonylative method using diaryl ketones to afford a variety of alkenylated heterocycles in good yields with moderate to good stereoselectivity and broad substrate scope. The synthetic utility of this protocol is also demonstrated by the conversion of the alkenylated heterocycles to tetrahydrocarbazole derivatives.

Key words

aryl migration - decarbonylation - unstrained ketones - Rh-catalysis - alkenylated heterocycles

• References

• 1a Dermenci A, Dong G. Sci. China: Chem. 2013; 56: 685
• 1b Lu H, Yu T.-Y, Xu P.-F, Wei H. Chem. Rev. 2021; 121: 365
• 2a Murakami M, Amii H, Shigeto K, Ito Y. J. Am. Chem. Soc. 1996; 118: 8285
• 2b Matsuda T, Shigeno M, Murakami M. Chem. Lett. 2006; 35: 288
• 3a Daugulis O, Brookhart M. Organometallics 2004; 23: 527
• 3b Lei Z.-Q, Li H, Li Y, Zhang X.-S, Chen K, Wang X, Sun J, Shi Z.-J. Angew. Chem. Int. Ed. 2012; 51: 2690
• 3c Morioka T, Nishizawa A, Furukawa T, Tobisu M, Chatani N. J. Am. Chem. Soc. 2017; 139: 1416
• 3d Zhao T.-T, Xu W.-H, Zheng Z.-J, Xu P.-F, Wei H. J. Am. Chem. Soc. 2018; 140: 586
• 3e Yu T.-Y, Xu W.-H, Lu H, Wei H. Chem. Sci. 2020; 11: 12336
• 4a Müller E, Segnitz A, Langer E. Tetrahedron Lett. 1969; 1129
• 4b Müller E, Segnitz A. Liebigs Ann. Chem. 1973; 1583
• 4c Kaneda K, Azuma H, Wayaku M, Tehanishi S. Chem. Lett. 1974; 3: 215
• 4d Dermenci A, Whittaker RE, Dong G. Org. Lett. 2013; 15: 2242
• 4e Dermenci A, Whittaker RE, Gao Y, Cruz FA, Yu Z.-X, Dong G. Chem. Sci. 2015; 6: 3201
• 4f Whittaker RE, Dong G. Org. Lett. 2015; 17: 5504
• 5 Golime G, Kim HY, Oh K. Org. Lett. 2018; 20: 942
• 6a Kondo T, Nakamura A, Okada T, Suzuki N, Wada K, Mitsudo T.-a. J. Am. Chem. Soc. 2000; 122: 6319
• 6b Kondo T, Taguchi Y, Kaneko Y, Niimi M, Mitsudo T.-a. Angew. Chem. Int. Ed. 2004; 43: 5369
• 6c Yamamoto Y, Kuwabara S, Hayashi H, Nishiyama H. Adv. Synth. Catal. 2006; 348: 2493
• 7a Xu T, Savage NA, Dong G. Angew. Chem. Int. Ed. 2014; 53: 1891
• 7b Zhou X, Zafar I, Dong G. Tetrahedron 2015; 71: 4478
• 7c Lu Q, Wang B, Yu H, Fu Y. ACS Catal. 2015; 5: 4881
• 7d Zhou X, Ko HM, Dong G. Angew. Chem. Int. Ed. 2016; 55: 13867
• 8 Chen P.-h, Xu T, Dong G. Angew. Chem. Int. Ed. 2014; 53: 1674
• 9a Zeng R, Dong G. J. Am. Chem. Soc. 2015; 137: 1408
• 9b Guo W, Wu S, Wang T, Xie Q, Duan Y, Luo S, Wang J, Yu X. Org. Chem. Front. 2018; 5: 1613
• 10 Zeng R, Chen P.-h, Dong G. ACS Catal. 2016; 6: 969
• 11 Shao P, Yu T, Lu H, Xu P.-F, Wei H. CCS Chem. 2020; 2: 1862
• 12 The role of acid may be to facilitate the process of β-H elimination with the formation of rhodium benzoate intermediate, see: Ishida M, Tanaka K. Org. Lett. 2013; 15: 2120
• 13 Tan G, Das M, Maisuls I, Strassert CA, Glorius F. Angew. Chem. Int. Ed. 2021; 60: 15650
• 14 Lu H, Zhao T.-T, Bai J.-H, Ye D, Xu P.-F, Wei H. Angew. Chem. Int. Ed. 2020; 59: 23537
• 15 Chen C.-B, Wang X.-F, Cao Y.-J, Cheng H.-G, Xiao W.-J. J. Org. Chem. 2009; 74: 3532
• 16 Yin L, Wang Y, Sun M, Shi F. Adv. Synth. Catal. 2016; 358: 1093
• 17 Zhang L, Qiu R, Xue X, Pan Y, Xu C, Wang D, Wang X, Xu L, Li H. Chem. Commun. 2014; 50: 12385
• 18 Shi L, Zhong X, She H, Lei Z, Li F. Chem. Commun. 2015; 51: 7136
• 19 Wang S, Hou J.-T, Feng M.-L, Zhang X.-Z, Chen S.-Y, Yu X.-Q. Chem. Commun. 2016; 52: 2709
• 20 Zhou B, Chen H, Wang C. J. Am. Chem. Soc. 2013; 135: 1264