Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**

Li，Sida1,3; Hu，Chenyang2; Cui，Xin1; Zhang，Jiong1,3; Liu，Liu Leo2; Wu，Lipeng1

2021

10.1002/anie.202111978

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

An unprecedented and general hydroboration of alkenes with BX (X=Br, Cl) as the boration reagent in the presence of PrNEt is reported. The addition of PrNEt not only suppresses alkene polymerization and haloboration side reactions but also provides an “H” source for hydroboration. More importantly, the site-fixed installation of a boryl group at the original position of the internal double bond is readily achieved in contrast to conventional transition-metal-catalyzed hydroboration processes. Further application to the synthesis of 1,n-diborylalkanes (n=3–10) is also demonstrated. Preliminary mechanistic studies reveal a major reaction pathway that involves radical species and operates through a frustrated Lewis pair type single-electron-transfer mechanism.

alkenes frustrated Lewis pairs hydroboration single-electron transfer

SCI ; EI

英语

NI期刊

通讯

National Natural Science Foundation of China[22101114,91845108,21901247,21902167] ; Natural Science Foundation of Jiangsu Province[BK20180246] ; SUSTech start-up fund[Y01216248]

Chemistry

Chemistry, Multidisciplinary

WOS:000714777500001

WILEY-V C H VERLAG GMBH

20214511118998

Electron transitions ; Free radical reactions ; Transition metals

Metallurgy and Metallography:531 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

2-s2.0-85118480652

Scopus

1.State Key Laboratory for Oxo Synthesis and Selective Oxidation,Suzhou Research Institute of LICP,Lanzhou Institute of Chemical Physics (LICP),Chinese Academy of Sciences,Lanzhou,730000,China
2.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
3.University of Chinese Academy of Sciences,Beijing,100049,China

Li，Sida,Hu，Chenyang,Cui，Xin,et al. Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60:26238-26245.

Li，Sida,Hu，Chenyang,Cui，Xin,Zhang，Jiong,Liu，Liu Leo,&Wu，Lipeng.(2021).Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60,26238-26245.

Li，Sida,et al."Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60(2021):26238-26245.