Journal
ACS CATALYSIS
Volume 6, Issue 4, Pages 2352-2356Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b00367
Keywords
cobalt catalysis; C-H bond activation; switchable selectivity; dehydrative cyclization; dehydrogenative cyclization
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Funding
- European Research Council under the European Community's Seventh Framework program/ERC Grant [25936]
- Alexander von Humboldt Foundation
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Achieving controllable CH functionalization to elaborate valuable compounds from simple chemicals is attractive and highly desirable, especially if nonprecious transition metal catalysts can be used. However, controlling selectivity in these transformations remains a continuous challenge to synthetic chemists. Herein, we show for the first time that control over the reactive organometallic intermediate enables the switchable synthesis of quinoline and indole from amides and alkynes through CH activation using Cp*Co(III). The keys to this strategy are (1) introducing a Lewis acid to greatly accelerate the dehydrative cyclization, which can outcompete dehydrogenative cyclization, and (2) tuning the directing group to facilitate the dehydrogenative cyclization and inhibit dehydrative cyclization.
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