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Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

ABSTRACT: An unprecedented redox-neutral annulation reaction of tertiary anilines with electron-deficient alkynes was developed that proceeds through a cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization sequence. Under B(C₆F₅)₃ catalysis, a range of functionalized 1,2,3,4-tetrahydroquinolines were facilely constructed in moderate to good yields with exclusive 3,4-anti-stereochemistry. The commercial availability of the catalyst and the high atom and step economy of the procedure, together with metal-free and external oxidant-free conditions, make this an attractive method in organic synthesis.

SUBMITTER: Zhang BB

PROVIDER: S-EPMC8768868 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

Zhang Bei-Bei BB Peng Shuo S Wang Feiyi F Lu Cuifen C Nie Junqi J Chen Zuxing Z Yang Guichun G Ma Chao C

Chemical science 20211220 3

An unprecedented redox-neutral annulation reaction of tertiary anilines with electron-deficient alkynes was developed that proceeds through a cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization sequence. Under B(C6F5)3 catalysis, a range of functionalized 1,2,3,4-tetrahydroquinolines were facilely constructed in moderate to good yields with exclusive 3,4-anti-stereochemistry. The commercial availability of the catalyst and the high ...[more]

PMID: 35173942

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