Citation: Yang Jimin, Li Ziqi, Zhu Shoufei. Progresses on the Application of Stable Borane Adducts in the Synthesis of Organoborons[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2481-2497. doi: 10.6023/cjoc201705034 shu

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

Corresponding author: Zhu Shoufei, sfzhu@nankai.edu.cn
Received Date: 23 May 2017
Revised Date: 18 July 2017
Available Online: 9 October 2017
Fund Project: the National Natural Science Foundation of China 21625204Project 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.the National Basic Research Program of China 2012CB821600the National Natural Science Foundation of China 21421062the National Natural Science Foundation of China 21290182the National Basic Research Program of China 973项目the “111” Project of the Ministry of Education of China B06005

Figures(29)

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.
- stable borane adduct,
- hydroboration,
- C—H bond borylation,
- B—H bond insertion,
- boryl radical
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