The functionalization of primary C-H bonds has been a longstanding challenge in catalysis. Our group has developed a series of silylations of primary C-H bonds that occur with site selectivity and diastereoselectivity resulting from an approach to run the reactions as intramolecular processes. These reactions have become practical by using an alcohol or amine as a docking site for a hydrosilyl group, thereby leading to intramolecular silylations of C-H bonds at positions dictated by the presence common functional groups in the reactants. Oxidation of the C-Si bond leads to the introduction of alcohol functionality at the position of the primary C-H bond of the reactant. The development, scope, and applications of these functionalization reactions is described in this minireview.
The functionalization of primary C-H bonds has been a longstanding challenge in catalyn class="Chemical">sis. Our group has developed a series of silylations of primary C-H bonds that occur with site selectivity and diastereoselectivity resulting from an approach to run the reactions as intramolecular processes. These reactions have become practical by using an alcohol or amine as a docking site for a hydrosilyl group, thereby leading to intramolecular silylations of C-H bonds at positions dictated by the presence common functional groups in the reactants. Oxidation of the C-Si bond leads to the introduction of alcohol functionality at the position of the primary C-H bond of the reactant. The development, scope, and applications of these functionalization reactions is described in this minireview.
Authors: Quentin Michaudel; Guillaume Journot; Alicia Regueiro-Ren; Animesh Goswami; Zhiwei Guo; Thomas P Tully; Lufeng Zou; Raghunath O Ramabhadran; Kendall N Houk; Phil S Baran Journal: Angew Chem Int Ed Engl Date: 2014-09-22 Impact factor: 15.336