Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes

Jin，Shengnan1; Li，Jinxia2; Liu，Kang1; Ding，Wei Yi2; Wang，Shuai1; Huang，Xiujuan1; Li，Xue1; Yu，Peiyuan2; Song，Qiuling1,3,4

2022-12-01

10.1038/s41467-022-31234-2

Nature Communications   Impact Factor & Quartile

2041-1723

Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development of chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack of direct synthetic protocols. Therefore, it is very challenging to develop a simple and effective strategy to obtain chiral 1,1-diborylalkanes. Herein, we develop an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes and highly enantioenriched gem-diborylalkanes were readily obtained. Our strategy uses simple terminal alkynes and two different boranes to construct valuable chiral gem-bis(boryl) alkanes with one catalytic and one ligand pattern, which represents the simplest and most straightforward strategy for constructing such chiral gem-diborons.

SCI

English

NI Journal Papers

Corresponding

National Outstanding Youth Science Fund Project of National Natural Science Foundation of China[21772046];National Outstanding Youth Science Fund Project of National Natural Science Foundation of China[21931013];

WOS:000813768100002

2-s2.0-85132288685

Scopus

1.Institute of Next Generation Matter Transformation,College of Material Sciences Engineering,Huaqiao University,Xiamen,Fujian,361021,China
2.Department of Chemistry and Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
3.School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang,Henan,453007,China
4.State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin,China

Jin，Shengnan,Li，Jinxia,Liu，Kang,et al. Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes[J]. Nature Communications,2022,13(1).

Jin，Shengnan.,Li，Jinxia.,Liu，Kang.,Ding，Wei Yi.,Wang，Shuai.,...&Song，Qiuling.(2022).Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.Nature Communications,13(1).

Jin，Shengnan,et al."Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes".Nature Communications 13.1(2022).