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Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols.

ABSTRACT: A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2?mol?%) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28?examples, 50-92?% yield, 79?% average yield).

SUBMITTER: Dambatta MB

PROVIDER: S-EPMC6619250 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols.

Dambatta Mubarak B MB Polidano Kurt K Northey Alexander D AD Williams Jonathan M J JMJ Morrill Louis C LC

ChemSusChem 20190507 11

A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50-92 % yield, 79 % average yield). ...[more]

PMID: 30958919

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