Main-group metalated heterocycles through Lewis acid cyclization

Autor: Suzanne A. Blum, Chao Gao
Rok vydání: 2021
Předmět:
Zdroj: Trends in Chemistry. 3:645-659
ISSN: 2589-5974
Popis: Main-group metalated heterocycles have broad applications in synthesis, drug development, and materials science. In this review, we highlight recent progress in synthesizing isolable main-group heterocycles of boron, indium, silicon, tin, selenium, and tellurium via Lewis acid cyclization pathways and discuss mechanistic insights. Different from traditional two-step synthetic routes in which heterocycles are constructed first followed by metalation, the herein-described Lewis acid cyclization reactions construct the heterocyclic core and install the metal in one synthetic step. These cyclization reactions proceed with predictable regioselectivity and with high functional group tolerance. While all the described reactions are Lewis acid cyclization reactions onto carbon–carbon π bonds, mechanistic studies show that different metals/reagents can proceed through different intermediates.
Databáze: OpenAIRE