Progresses on the Application of Stable Borane Adducts in the Synthesis of Organoborons

doi:10.6023/cjoc201705034

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2481-2497.DOI: 10.6023/cjoc201705034 Previous Articles Next Articles

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稳定硼烷加合物在有机硼化物合成中的应用研究进展

杨吉民^a, 李子奇^a, 朱守非^a,b

a 南开大学化学学院元素有机化学研究所元素有机化学国家重点实验室天津 300071;
b 天津化学化工协同创新中心天津 300071

收稿日期:2017-05-23 修回日期:2017-07-18 发布日期:2017-08-09
通讯作者: 朱守非 E-mail:sfzhu@nankai.edu.cn
基金资助:
国家自然科学基金（Nos.21625204，21421062，21290182）、国家重点基础研究发展计划（973项目，No.2012CB821600）、教育部"111计划"（No.B06005）和国家特支计划资助项目.

Progresses on the Application of Stable Borane Adducts in the Synthesis of Organoborons

Yang Jimin^a, Li Ziqi^a, Zhu Shoufei^a,b

a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071;
b Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071

Received:2017-05-23 Revised:2017-07-18 Published:2017-08-09
Contact: 10.6023/cjoc201705034 E-mail:sfzhu@nankai.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21625204,21421062,21290182),the National Basic Research Program of China (973 Program,No.2012CB821600),the "111" Project of the Ministry of Education of China (No.B06005),and the National Program for Support of Top-notch Young Professionals.

Organoboron compounds are wildly used in organic synthesis, materials science, life and health science, etc. The development of synthetic methodologies of organoborons has therefore gained intense attention nowadays. Typically, Bis(pinacolato)diboron (B₂Pin₂), pinacolborane (HBpin) and catecholatoborane (HBCat) are predominantly used as boron reagents in catalytic C-B bond forming reactions. Different from the above traditional boron reagents, borane adducts with strong Lewis bases, such as amines, phosphines, and N-heterocyclic carbenes, are promising boron reagents because of their readily accessibility, relatively high stability, and easy operation. Moreover, the different chemical properties of these stable borane adducts towards the traditional boron reagents provide possibilities for development of new C-B bond formation reactions. The applications of the stable borane adducts as terminal boron reagents in hydroboration of alkenes or alkynes, C-H bond borylation, carbene insertion into B-H bonds, cascade cyclization initiated by boryl radicals and substitutions, which provide new methods for the preparation of organoborons are reviewed in this paper.

Key words: stable borane adduct, hydroboration, C—H bond borylation, B—H bond insertion, boryl radical

Cite this article

Yang Jimin, Li Ziqi, Zhu Shoufei. Progresses on the Application of Stable Borane Adducts in the Synthesis of Organoborons[J]. Chin. J. Org. Chem., 2017, 37(10): 2481-2497.

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稳定硼烷加合物在有机硼化物合成中的应用研究进展

Progresses on the Application of Stable Borane Adducts in the Synthesis of Organoborons

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