Rhodium(II)-catalyzed multicomponent assembly of α,α,α-trisubstituted esters via formal insertion of O–C(sp3)–C(sp2) into C–C bonds

Dan Ba, Si Wen, Qingyu Tian, Yanhui Chen, Weiwei Lv and Guolin Cheng ()
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Dan Ba: Huaqiao University
Si Wen: Huaqiao University
Qingyu Tian: Huaqiao University
Yanhui Chen: Huaqiao University
Weiwei Lv: Huaqiao University
Guolin Cheng: Huaqiao University

Nature Communications, 2020, vol. 11, issue 1, 1-6

Abstract: Abstract The direct cleavage of C(CO)−C single bonds, delivering otherwise inaccessible compounds, is a significant challenge. Although the transition metal-catalyzed insertion of functional groups into C(CO)−C bonds has been studied, strained ketone substrates or chelating assistance were commonly required. In this article, we describe a rhodium(II)-catalyzed three-component reaction of 1,3-diones, diazoesters, and N,N-dimethylformamide (DMF), leading to an unusual formal insertion of O–C(sp3)–C(sp2) into unstrained C(CO)−C bonds. This procedure provides a rapid entry to a gamut of otherwise inaccessible α,α,α-trisubstituted esters/amide from relatively simple substrates in a straightforward manner. 55 examples of highly decorated products demonstrate the broad functional group tolerance and substrate scope. The combination of control experiments and isotope-labeling reactions support that O, C(sp3), and C(sp2) units derive from 1,3-diones, diazoesters, and DMF, respectively.

Date: 2020
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DOI: 10.1038/s41467-020-17990-z

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