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Unified synthesis of multiply arylated alkanes by catalytic deoxygenative transformation of diarylketones.

ABSTRACT: A deoxygenative transformation of diarylketones leading to multiply arylated alkanes was developed. Diarylketones were reacted with diphenylphosphine oxide resulting in a phospha-Brook rearrangement, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation to afford the corresponding multiply arylated alkanes. A variety of diarylketones can be converted to multiply arylated alkanes such as diarylmethanes, tetraarylethanes, and triarylmethanes by reduction, dimerization, and arylation in one pot. Furthermore, a one-pot conversion from arylcarboxylic acids to diarylmethanes and tetraarylethanes, and a synthesis of tetraarylmethane and triphenylethane using sequential coupling reactions are also presented.

SUBMITTER: Kurosawa MB

PROVIDER: S-EPMC9491083 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Unified synthesis of multiply arylated alkanes by catalytic deoxygenative transformation of diarylketones.

Kurosawa Miki B MB Kato Kenta K Muto Kei K Yamaguchi Junichiro J

Chemical science 20220822 36

A deoxygenative transformation of diarylketones leading to multiply arylated alkanes was developed. Diarylketones were reacted with diphenylphosphine oxide resulting in a phospha-Brook rearrangement, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation to afford the corresponding multiply arylated alkanes. A variety of diarylketones can be converted to multiply arylated alkanes such as diarylmethanes, tetraarylethanes, and triarylmethanes by reduction, dimerization ...[more]

PMID: 36320688

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