Esters as Radical Acceptors: β-NHC-Borylalkenyl Radicals Induce Lactonization by C−C Bond Formation/Cleavage on Esters
- Award ID(s):
- 1660927
- PAR ID:
- 10108582
- Date Published:
- Journal Name:
- Angewandte Chemie International Edition
- Volume:
- 58
- Issue:
- 19
- ISSN:
- 1433-7851
- Page Range / eLocation ID:
- 6357 to 6361
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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In the past several years, tremendous advances have been made in non-classical routes for amide bond formation that involve transamidation and amidation reactions of activated amides and esters. These new methods enable the formation of extremely valuable amide bonds via transition-metal- catalyzed, transition-metal-free or metal-free pathways by exploiting chemoselective acyl C–X (X = N, O) cleavage under mild conditions. In a broadest sense, these reactions overcome the formidable challenge of activating C–N/C–O bonds of amides or esters by rationally tackling nN→π*C=O delocalization in amides and nO→π*C=O donation in esters. In this account, we summarize the recent remarkable advances in the development of new methods for the synthesis of amides with a focus on (1) transition-metal/NHC- catalyzed C–N/C–O bond activation, (2) transition-metal-free highly selective cleavage of C–N/C–O bonds, (3) the development of new acyl-transfer reagents, and (4) other emerging methods.more » « less
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