Citation: Lu Wang, Wei Sun, Chao Liu. Cu-catalyzed deoxygenative gem-hydroborylation of aromatic aldehydes and ketones to access benzylboronic esters[J]. Chinese Journal of Catalysis, ;2018, 39(11): 1725-1729. doi: 10.1016/S1872-2067(18)63139-0 shu

Cu-catalyzed deoxygenative gem-hydroborylation of aromatic aldehydes and ketones to access benzylboronic esters

Lu Wang ^a, ,
Wei Sun ^a,b ,
Chao Liu ^a

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of Lanzhou Institute of Chemical Physics(LICP), LICP, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received Date: 13 June 2018
Revised Date: 15 July 2018

Fund Project: This work was supported by the National Natural Science Foundation of China (91745110, 21673261, 21603245, 21633013, 21703265) and a Start-up funding from LICP. Support from the Young Elite Scientist Sponsorship Program by CAST, CAS Interdisciplinary Innovation Team, the Key Program of CAS (QYZDJ-SSW-SLH051), the Youth Innovation Promotion Association CAS (2018458) and the ‘Light of West China’ Program.

Organoboron compounds are widely used in synthetic chemistry, pharmaceutical chemistry and material chemistry. Among various organoboron compounds, benzylboronic esters are unique and highly reactive, making them suitable benzylation reagents. At present, the synthetic methods for the syntheses of benzylboronic esters are still insufficient to meet their demands. It is necessary to develop novel and practical methods for their preparation. In this work, a novel copper-catalyzed deoxygenative gem-hydroborylation of aromatic aldehydes and ketones has been developed. This direct and operationally simple protocol provides an effective approach for the synthesis of a variety of primary and secondary benzylboronates, in which broad functional group tolerance was presented. Widely available B₂pin₂ (pin=pinacol) was used as the boron source and alcoholic proton was applied as the hydride source.
- Homogeneous catalysis,
- Copper catalysis,
- Deoxygenative gem-hydroborylation,
- Aromatic aldehydes,
- Aromatic ketones
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