TY - JOUR
T1 - Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C-Si Bonds
AU - Gandhamsetty, Narasimhulu
AU - Park, Sehoon
AU - Chang, Sukbok
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/12/9
Y1 - 2015/12/9
N2 - Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp3 C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.
AB - Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp3 C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.
UR - http://www.scopus.com/inward/record.url?scp=84949604664&partnerID=8YFLogxK
U2 - 10.1021/jacs.5b09209
DO - 10.1021/jacs.5b09209
M3 - 文章
AN - SCOPUS:84949604664
SN - 0002-7863
VL - 137
SP - 15176
EP - 15184
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 48
ER -