Boron-Catalyzed Aromatic C–H Bond Silylation with Hydrosilanes

Abstract

Metal-free catalytic C-H silylation of a series of aromatic compounds such as N,N-disubstituted anilines with various hydrosilanes has been achieved for the first time using commercially available B(C6F5)3 as a catalyst. This protocol features simple and neutral reaction conditions, high regioselectivity, wide substrate scope (up to 40 examples), Si-Cl bond compatibility, and no requirement for a hydrogen acceptor.

Aryl(triethyl)silanes for Biaryl and Teraryl Synthesis by Copper(II)‐Catalyzed Cross‐Coupling Reaction

“…Thef ive-membered heterocycle,2 -triethylsilylbenzo[b]thiophene (6a), cross-coupled with 4a, 4m,or6-iodoquinoline (4n), smoothly to give the corresponding coupled product 7aa, 7am,or7an (Entries 8-10). (2)]. Use of 3,5- bis(trifluoromethyl)phenyl(triethyl)silane (6c)g ave biaryl 7ca in amoderate yield (Entry 12).…”

Recent Progress in the Cross-Coupling Reaction Using Triorgano­silyl-Type Reagents

“…32 This type of transformation is made possible by C-H silylation of arenes catalyzed by a transition-metal complex, 33 t-BuOK, 34 B(C 6 F 5 ) 3 , 35 or a Brønsted acid.…”

Electrophilic Aromatic Substitution with Silicon Electrophiles: Catalytic Friedel–Crafts C−H Silylation

“…[23] Ab road range of anilines underwent the C À Hs ilylation even in the absence of base (30!31). [23] Ab road range of anilines underwent the C À Hs ilylation even in the absence of base (30!31).…”