Journal
ORGANIC LETTERS
Volume 24, Issue 36, Pages 6525-6530Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02420
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Funding
- NIH [1R35GM133719-01]
- Sloan Foundation
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The site-selective reaction at a specific C-N amide bond is a challenging task. By using twisted amides and electronic activation, a particular amide bond can be selectively activated for C-C bond formation even in the presence of similar amides.
The chemo- and site-selective reaction at the particular C-N amide bond among a sea of other amides is a significant and long-standing challenge. Although the use of twisted amides has been demonstrated for modifications of inert C-N amide bonds, none of these methods can selectively activate a particular amide bond for C-C bond formation in the presence of similar amides. Using density functional theory as a guide, we report the first site-selective C-C bond modification of a particular C-N amide bond in polyamides with a low twist angle by combining ground-state steric distortion with electronic activation.
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