Reaction of 4-Bpin-o-Carborane with Ketones: Sequential Carbon Vertex Alkylation and B−B Bond Activation

Nie，Zhen1; Cheng，Ruofei1; Qiu，Zaozao1,2; Xie，Zuowei1,3,4

2023-09-15

10.1002/asia.202300598

Chemistry - An Asian Journal   Impact Factor & Quartile

1861-4728

1861-471X

Diboron compounds are important reagents in a series of transition metal catalyzed or metal-free borylation reactions. We describe herein a unique reactivity of 4-Bpin-o-carborane with ketones under basic conditions, leading to sequential cage carbon alkylation, B−B bond activation and unexpected O-migration. The reaction was compatible with a good substrate scope including dialkyl or alkyl aryl ketones. The reaction mechanism is also proposed, involving cage CH deprotonation, nucleophilic attack of ketone, and O-migration along with B−B bond cleavage.

B−B bond activation carborane diboron compound ketone O-migration

SCI

English

Corresponding

National Natural Science Foundation of China[92056106 to Z.Q.];

Chemistry

Chemistry, Multidisciplinary

WOS:001049679600001

WILEY-V C H VERLAG GMBH

2-s2.0-85168288893

Scopus

1.Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai,345 Lingling Rd,200032,China
2.School of Chemistry and Materials Science,Hangzhou Institute for Advanced Study,University of Chinese Academy of Sciences,Hangzhou,1 Sub-lane Xiangshan,310024,China
3.Department of Chemistry,The Chinese University of Hong Kong,Shatin, N. T.,Hong Kong
4.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China

Nie，Zhen,Cheng，Ruofei,Qiu，Zaozao,et al. Reaction of 4-Bpin-o-Carborane with Ketones: Sequential Carbon Vertex Alkylation and B−B Bond Activation[J]. Chemistry - An Asian Journal,2023,18(18).

Nie，Zhen,Cheng，Ruofei,Qiu，Zaozao,&Xie，Zuowei.(2023).Reaction of 4-Bpin-o-Carborane with Ketones: Sequential Carbon Vertex Alkylation and B−B Bond Activation.Chemistry - An Asian Journal,18(18).

Nie，Zhen,et al."Reaction of 4-Bpin-o-Carborane with Ketones: Sequential Carbon Vertex Alkylation and B−B Bond Activation".Chemistry - An Asian Journal 18.18(2023).