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
收藏
页码：1101 / 1106
页数：6
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