TY - JOUR
T1 - Regioselective Nucleophilic Alkylation/Arylation of B–H Bonds in o-Carboranes
T2 - An Alternative Method for Selective Cage Boron Functionalization
AU - Tang, Cen
AU - Zhang, Jiji
AU - Zhang, Jie
AU - Xie, Zuowei
N1 - Publisher Copyright:
© 2018 American Chemical Society.
Funding Information:
This work was supported by grants from the Research Grants Council of The Hong Kong Special Administration Region (Project 14305918) and an Incentive Grant from Faculty of Science, CUHK
PY - 2018/12/5
Y1 - 2018/12/5
N2 - A new protocol for regioselective nucleophilic cage B–H substitution in o-carboranes has been proposed that is complementary to the strategies of transition metal catalysis and electrophilic substitution. Magnesium-mediated site-selective nucleophilic cage B(3,6)–H and B(9)–H substitution reactions of o-carboranes give a series of B(3,6)-dialkylated and B(9)-alkylated/arylated o-carboranes in high yields. Both steric and electronic factors of cage C substituents play crucial roles in controlling the site selectivity.
AB - A new protocol for regioselective nucleophilic cage B–H substitution in o-carboranes has been proposed that is complementary to the strategies of transition metal catalysis and electrophilic substitution. Magnesium-mediated site-selective nucleophilic cage B(3,6)–H and B(9)–H substitution reactions of o-carboranes give a series of B(3,6)-dialkylated and B(9)-alkylated/arylated o-carboranes in high yields. Both steric and electronic factors of cage C substituents play crucial roles in controlling the site selectivity.
UR - https://www.scopus.com/pages/publications/85058075651
U2 - 10.1021/jacs.8b10270
DO - 10.1021/jacs.8b10270
M3 - Journal article
C2 - 30441890
AN - SCOPUS:85058075651
SN - 0002-7863
VL - 140
SP - 16423
EP - 16427
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 48
ER -
