Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane

被引：82
|
作者：
Wang, Chao [1 ]
Wu, Caizhi [1 ]
Ge, Shaozhong [1 ]
机构：
[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
来源：
ACS CATALYSIS | 2016年 / 6卷 / 11期
关键词：
iron; borylation; dehydrogenative; vinylarenes; homogeneous catalysis; OLEFIN CROSS-METATHESIS; C-H BORYLATION; ALKENE HYDROBORATION; HYDRIDE COMPLEXES; ALPHA-ARYLATION; B-H; ALKYNES; 1,3-DIENES; EFFICIENT; LIGAND;
D O I：
10.1021/acscatal.6b02654
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
We report the dehydrogenative borylation of vinylarenes with pinacolborane (HBpin) catalyzed by an iron(0) complex "(PMe3)(4)Fe". A variety of monosubstituted and disubstituted vinylarenes underwent this iron-catalyzed transformation, affording E-vinyl boronate esters (VBEs) selectively in high yields. In addition, we coupled this iron-catalyzed dehydrogenative borylation with further transformations of the resulting vinyl boronate esters and developed various one-pot procedures for the functionalization of the vinylic C-H bonds in vinylarenes. Mechanistic studies reveal that this Fe-catalyzed reaction proceeds through syn-insertion of vinylarenes into a Fe-boryl species followed by beta-hydrogen elimination from a syn coplanar conformation of the borylalkyl iron intermediate.
引用
收藏
页码：7585 / 7589
页数：5
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