Iron-Catalyzed Deoxygenative Diborylation of Ketones to Internal gem-Diboronates

doi:10.6023/cjoc201909008

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3438-3445.DOI: 10.6023/cjoc201909008 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

铁催化酮类化合物脱氧双硼化制备非末端偕二硼

何泽瑜^a,b, 范敏^a, 徐佳能^a,b, 胡越^a, 王露^a, 吴旭东^a,c, 夏春谷^a, 刘超^a

a 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室兰州 730000;
b 中国科学院大学北京 100049;
c 宜宾学院化学与化工学院四川宜宾 644007

收稿日期:2019-09-06 修回日期:2019-09-18 发布日期:2019-09-25
通讯作者: 刘超 E-mail:chaoliu@licp.cas.cn
基金资助:
国家自然科学基金（Nos.91745110，21673261，21603245，21633013，21703265，21872156，21802150）、江苏省自然科学基金（Nos.BK20181194，BK20180247）、中国科协青年人才托举工程（No.YESS20170217）和中国科学院青年创新促进会（No.2018458）资助项目.

Iron-Catalyzed Deoxygenative Diborylation of Ketones to Internal gem-Diboronates

He Zeyu^a,b, Fan Min^a, Xu Jia'neng^a,b, Hu Yue^a, Wang Lu^a, Wu Xudong^a,c, Xia Chungu^a, Liu Chao^a

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000;
b University of Chinese Academy of Sciences, Beijing 100049;
c Department of Chemistry and Chemical Engineering, Yibin University, Yibin, Sichuan 644007

Received:2019-09-06 Revised:2019-09-18 Published:2019-09-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 91745110, 21673261, 21603245, 21633013, 21703265, 21872156, 21802150), the Natural Science Foundation of Jiangsu Province (Nos. BK20181194, BK20180247), the Young Elite Scientist Sponsorship Program by China Association for Science and Technology (No. YESS20170217) and the Youth Innovation Promotion Association of Chinese Academy of Sciences (No. 2018458).

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Abstract

An iron catalyzed deoxygenative diborylation of ketones to access a variety of internal gem-diboronates has been developed. A scale-up synthesis of such gem-diboronates is also applicable under this condition. Meanwhile, common organic solvent acetone was used as start material to synthesize corresponding internal gem-diboronate, and further mono- or di-functionalization of such internal gem-diboronate has also been explored to demonstrate the synthetic potential of internal gem-diboronates.

Key words: iron catalysis, aliphatic ketone, deoxygenative borylation, gem-diboronate

Cite this article

He Zeyu, Fan Min, Xu Jia'neng, Hu Yue, Wang Lu, Wu Xudong, Xia Chungu, Liu Chao. Iron-Catalyzed Deoxygenative Diborylation of Ketones to Internal gem-Diboronates[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3438-3445.

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铁催化酮类化合物脱氧双硼化制备非末端偕二硼

Iron-Catalyzed Deoxygenative Diborylation of Ketones to Internal gem-Diboronates

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