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Practical, metal-free remote heteroarylation of amides via unactivated C(sp³)-H bond functionalization.

ABSTRACT: Development of practical methods for the production of multi-functionalized amides is one of the most important topics in both synthetic chemistry and drug discovery. Disclosed herein is a new, efficient, site-selective heteroarylation of amides via C(sp³)-H bond functionalization. Amidyl radicals are directly generated from the amide N-H bonds under mild conditions, which trigger the subsequent 1,5-HAT process. A wide scope of aliphatic amides including carboxamides, sulfonamides, and phosphoramides are readily modified at remote C(sp³)-H bonds by installing diverse heteroaryl groups. Borne out of pragmatic consideration, this protocol can be used for the late-stage functionalization of amides.

SUBMITTER: Tang N

PROVIDER: S-EPMC6640195 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Practical, metal-free remote heteroarylation of amides via unactivated C(sp3)-H bond functionalization.

Tang Nana N Wu Xinxin X Zhu Chen C

Chemical science 20190611 28

Development of practical methods for the production of multi-functionalized amides is one of the most important topics in both synthetic chemistry and drug discovery. Disclosed herein is a new, efficient, site-selective heteroarylation of amides via C(sp3)-H bond functionalization. Amidyl radicals are directly generated from the amide N-H bonds under mild conditions, which trigger the subsequent 1,5-HAT process. A wide scope of aliphatic amides including carboxamides, sulfonami ...[more]

PMID: 31391914

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