期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 3, 页码 1116-1150出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913645
关键词
convergence; fragment coupling; radical chemistry; total synthesis
资金
- Yale University
Fragment coupling reactions that form carbon-carbon bonds are important transformations in synthetic design. In recent years, there has been an increase in fragment couplings proceeding via carbanionic and open-shell intermediates. These reactions provide predictability and reliability, while also offering valuable lessons for students.
Fragment coupling reactions that form carbon-carbon bonds are valuable transformations in synthetic design. Advances in metal-catalyzed cross-coupling reactions in the early 2000s brought a high level of predictability and reliability to carbon-carbon bond constructions involving the union of unsaturated fragments. By comparison, recent years have witnessed an increase in fragment couplings proceeding via carbanionic and open-shell (free radical) intermediates. The latter has been driven by advances in methods to generate and utilize carbon-centered radicals under mild conditions. In this Review, we survey a selection of recent syntheses that have implemented carbanion- or radical-based fragment couplings to form carbon-carbon bonds. We aim to highlight the strategic value of these disconnections in their respective settings and to identify extensible lessons from each example that might be instructive to students.
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