Catalytic Dearomatization of N-Heteroarenes with Silicon and Boron Compounds.
Dearomatized N-heterocycles are an important class of structural motifs for organic synthesis and chemical biology. The catalytic dearomative reduction of unactivated N-heteroarenes using silicon and/or boron-containing compounds as a reductant is one of the most straightforward alternatives to hydrogenation. However, thus far, there are few reported examples on the catalytic reduction of N-heteroaromatic compounds with silane or borane reducing agents. This Review presents recent advances in the catalytic reduction of unactivated N-heteroarenes by hydrosilanes, hydroboranes, silaboranes, and diboranes. The focus is on the chemical reactivity and selectivity of transition-metal or metal-free organocatalyst systems. In addition, the working modes of these catalysis will be described primarily on the basis of experimental mechanistic insight.
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science, IBS, Daejeon, 305-701, South Korea.|Department of Chemistry, Korea Advanced Institute of Science & Technology, KAIST, Daejeon, 305-701, South Korea.
Sehoon
S
Park
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science, IBS, Daejeon, 305-701, South Korea.|Department of Chemistry, Korea Advanced Institute of Science & Technology, KAIST, Daejeon, 305-701, South Korea.
Sukbok
S
Chang
N-heteroarenes; boration; catalytic reduction; dearomatization; silylation