Sequential Protocol for C(sp3)–H Carboxylation with CO2: Transition-Metal-Catalyzed Benzylic C–H Silylation and Fluoride-Mediated Carboxylation
- 19 June 2012
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (13), 3462-3465
- https://doi.org/10.1021/ol301431d
Abstract
One of the most challenging transformations in current organic chemistry is the catalytic carboxylation of a C(sp(3))-H bond using CO(2) gas, an inexpensive and ubiquitous C1 source. A sequential protocol for C(sp(3))-H carboxylation by employing a nitrogen-directed, metal-assisted, C-H activation/catalytic silylation reaction in conjunction with fluoride-mediated carboxylation with CO(2) was established. The carboxylation proceeded only at the benzylic C(sp(3))-Si bond, not at the aromatic C(sp(2))-Si, which is advantageous for further manipulations of the products.Keywords
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