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Synthesis of Dihydroindolooxazines via a Redox-Neutral, Gold-Catalyzed Hydride-Transfer Process

Year: 2026

Type: article

Abstract: Redox-neutral gold-mediated processes are particularly valuable for C–H bond functionalization. When these transformations proceed stepwise via intramolecular hydride transfer to an electrophilic gold(I) center, their efficiency critically depends on the nature of the hydride donor. We report herein that, in contrast to tertiary amines, which strongly coordinate to gold and thereby tend to inhibit catalysis, benzyl ethers can serve as effective hydride donors, enabling a smooth catalytic C–H functionalization sequence. This reactivity is illustrated by the synthesis of a series of dihydroindolooxazines, obtained in moderate to high yields under mild catalytic conditions.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c04171

Authors: Elyssa Caron, Fabien Gagosz

Institution: University of Ottawa

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of Ottawa, Government of Canada, Alliance de recherche numérique du Canada, Natural Sciences and Engineering Research Council of Canada

OpenAlex ID: W7213979896

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