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Functionalization of α-C(sp³ )-H Bonds in Amides Using Radical Translocating Arylating Groups.

ABSTRACT: α-C-H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp³ )-H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO₂ extrusion.

SUBMITTER: Radhoff N

PROVIDER: S-EPMC7898318 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Functionalization of α-C(sp3 )-H Bonds in Amides Using Radical Translocating Arylating Groups.

Radhoff Niklas N Studer Armido A

Angewandte Chemie (International ed. in English) 20201230 7

α-C-H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3 )-H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequen ...[more]

PMID: 33215815

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