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Enantioselective nickel-catalyzed dicarbofunctionalization of 3,3,3-trifluoropropene.

ABSTRACT: Despite paramount applications of chiral trifluoromethylated compounds in medicinal chemistry and materials science, limited strategies have been developed for catalytic asymmetric synthesis of such valuable fluorinated structures. Here, we report a nickel catalyzed enantioselective dicarbofunctionalization of inexpensive industrial chemical 3,3,3-trifluoropropene (TFP) with readily available tertiary alkyl and aryl iodides. The reaction overcomes the β-F elimination side reaction of TFP, and proceeds efficiently under mild reaction conditions. The protocol possesses advantages, such as synthetic convenience, high enantioselectivity, and excellent functional group tolerance, providing rapid and straightforward access to chiral trifluoromethylated compounds of medicinal interest.

SUBMITTER: Li YZ

PROVIDER: S-EPMC9492779 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Enantioselective nickel-catalyzed dicarbofunctionalization of 3,3,3-trifluoropropene.

Li Yun-Ze YZ Rao Na N An Lun L Wan Xiao-Long XL Zhang Yanxia Y Zhang Xingang X

Nature communications 20220921 1

Despite paramount applications of chiral trifluoromethylated compounds in medicinal chemistry and materials science, limited strategies have been developed for catalytic asymmetric synthesis of such valuable fluorinated structures. Here, we report a nickel catalyzed enantioselective dicarbofunctionalization of inexpensive industrial chemical 3,3,3-trifluoropropene (TFP) with readily available tertiary alkyl and aryl iodides. The reaction overcomes the β-F elimination side reaction of TFP, and pr ...[more]

PMID: 36130927

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