Selective synthesis of secondary benzylic (Z)-allylboronates by Fe-catalyzed 1,4-hydroboration of 1-aryl-substituted 1,3-dienes

被引：43

作者：

Cao, Yanchun ^{[1
]}

Zhang, Yanlu ^{[1
]}

Zhang, Lei ^{[1
]}

Zhang, Dan ^{[1
]}

Leng, Xuebing ^{[1
]}

Huang, Zheng ^{[1
]}

机构：

[1] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 09期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; EFFICIENT ROUTE; BORONIC ESTERS; ALKENE HYDROBORATION; ALLYLIC CARBONATES; ALLYLBORONIC ACIDS; HYDROXY GROUP; IRON; ALCOHOLS; ARYL;

D O I：

10.1039/c4qo00206g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have prepared and characterized a series of new iminopyridine iron complexes with a bulky diphenyl-phosphinomethyl-ketimine substituent. Using one of these iron complexes as the precatalyst, the hydroboration of 1-substituted 1,3-dienes containing aromatic groups with pinacolborane occurs regio- and stereoselectively to form secondary (Z)-allylboronates. In addition, we report the first examples of Suzuki-Miyaura cross-coupling of secondary allylboronates with aryl bromides. The reactions catalyzed by Pd(dba)(2)/Ad(2)PnBu yield the coupling products with excellent regioselectivity (gamma/alpha > 99 : 1) and E-selectivity of the olefin geometry (E/Z > 99 : 1).

引用

页码：1101 / 1106

页数：6

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