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Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon-Carbon Bonds.

ABSTRACT: A rhodium-catalyzed direct insertion of ethylene into a relatively unstrained carbon-carbon bond in 1-indanones is reported, which provides a two-carbon ring expansion strategy for preparing seven-membered cyclic ketones. As many 1-indanones are commercially available and ethylene is inexpensive, this strategy simplifies synthesis of benzocycloheptenones that are valuable synthetic intermediates for bioactive compounds but challenging to prepare otherwise. In addition, the reaction is byproduct-free, redox neutral, and tolerant of a wide range of functional groups, which may have implications on unconventional strategic bond disconnections for preparing complex cyclic molecules.

SUBMITTER: Xia Y

PROVIDER: S-EPMC7075334 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon-Carbon Bonds.

Xia Ying Y Ochi Shusuke S Dong Guangbin G

Journal of the American Chemical Society 20190808 33

A rhodium-catalyzed direct insertion of ethylene into a relatively unstrained carbon-carbon bond in 1-indanones is reported, which provides a two-carbon ring expansion strategy for preparing seven-membered cyclic ketones. As many 1-indanones are commercially available and ethylene is inexpensive, this strategy simplifies synthesis of benzocycloheptenones that are valuable synthetic intermediates for bioactive compounds but challenging to prepare otherwise. In addition, the reaction is byproduct- ...[more]

PMID: 31389237

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