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Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles.

ABSTRACT: The Lewis acid-promoted phosphorylation of 2-indolylmethanols with diarylphosphine oxides is described. The regioselectivity of the reaction can be modulated by the choice of rare earth metal Lewis acid, offering a highly selective approach to structurally diverse indole derivatives in up to 97% yield for over 50 examples. This strategy features high selectivity, good functional group tolerance, and easy scalability. The utility of this method is further highlighted by facile modification of the products to access novel indole-based phosphine ligand.

SUBMITTER: Hu C

PROVIDER: S-EPMC5972529 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles.

Hu Chen C Hong Gang G He Yuchen Y Zhou Chen C Kozlowski Marisa C MC Wang Limin L

The Journal of organic chemistry 20180404 8

The Lewis acid-promoted phosphorylation of 2-indolylmethanols with diarylphosphine oxides is described. The regioselectivity of the reaction can be modulated by the choice of rare earth metal Lewis acid, offering a highly selective approach to structurally diverse indole derivatives in up to 97% yield for over 50 examples. This strategy features high selectivity, good functional group tolerance, and easy scalability. The utility of this method is further highlighted by facile modification of the ...[more]

PMID: 29605995

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