Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 42, Pages 12664-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja075785o
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Sequential cross-coupling on multihalogenated heterocycles is a particularly attractive strategy for the divergent synthesis of polysubstituted heterocycles, but the factors that govern the regioselectivity are not well understood. The present study shows that the selectivity in palladium-catalyzed cross-coupling reactions of heterocycles bearing multiple identical halogens is determined by both the energy to distort the carbon halogen bond to the transition-state geometry (related to BDE) and the interaction of the heterocycle pi* (LUMO) and PdL2 HOMO.
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