Nickel-catalyzed regioselective B(3,4,5,6)-H tetra-alkylation of o-carboranes

Zhao，Jianwei1; Xie，Zuowei1,2

2023

10.1007/s11426-023-1750-0

Science China Chemistry   影响因子和分区

1674-7291

1869-1870

Though transition metal-catalyzed cage BH methylation has been well documented, catalytic alkylation of cage BH bonds remained elusive because transition metal alkyl complexes are prone to undergo ß-H elimination. We report herein a highly efficient 8-aminoquinoline-assisted nickel-catalyzed regioselective cage B(3,4,5,6)-H tetra-alkylation of o-carboranes employing unactivated alkyl bromides as alkylating agents in the absence of any oxidants, leading to the preparation of a class of tetra-alkylated o-carboranes with a broad substrate scope in good to very high yields. This method opens new avenues for oxidant-free, direct, efficient, sustainable, and regioselective multiple B–H alkylation of carboranes via base metal catalysis.

alkylation B–H activation carborane nickel catalysis regioselectivity

SCI ; EI

英语

通讯

Research Grants Council of the Hong Kong Special Administration Region[SRFS2021-4S05]

Chemistry

Chemistry, Multidisciplinary

WOS:001063959400001

SCIENCE PRESS

20233614696012

Catalysis ; Nickel ; Oxidants ; Regioselectivity

Nickel:548.1 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803

2-s2.0-85169885764

Scopus

1.Department of Chemistry and State Key Laboratory of Synthetic Chemistry,The Chinese University of Hong Kong,999077,Hong Kong
2.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China

Zhao，Jianwei,Xie，Zuowei. Nickel-catalyzed regioselective B(3,4,5,6)-H tetra-alkylation of o-carboranes[J]. Science China Chemistry,2023,66(10):2836-2841.

Zhao，Jianwei,&Xie，Zuowei.(2023).Nickel-catalyzed regioselective B(3,4,5,6)-H tetra-alkylation of o-carboranes.Science China Chemistry,66(10),2836-2841.

Zhao，Jianwei,et al."Nickel-catalyzed regioselective B(3,4,5,6)-H tetra-alkylation of o-carboranes".Science China Chemistry 66.10(2023):2836-2841.