Sequential protocol for C(sp3)-H carboxylation with CO2: transition-metal-catalyzed benzylic C-H silylation and fluoride-mediated carboxylation |
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Authors: | Mita Tsuyoshi Michigami Kenichi Sato Yoshihiro |
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Affiliation: | Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. tmita@pharm.hokudai.ac.jp |
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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. |
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