钯催化二溴代化合物自偶联环化合成二苯并[a,e]环辛四烯

doi:10.1016/S1872-2067(14)60201-1

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 24-32.DOI: 10.1016/S1872-2067(14)60201-1

钯催化二溴代化合物自偶联环化合成二苯并[a,e]环辛四烯

欧阳昆冰^a,b, 席振峰^b

a 北京分子科学国家实验室(筹), 中国科学院化学研究所, 北京100190;
b 北京分子科学国家实验室(筹), 北京大学化学学院, 生物有机与分子工程教育部重点实验室, 北京100871

收稿日期:2014-06-30 修回日期:2014-07-21 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 席振峰
基金资助:
国家重点基础研究发展计划(973计划, 2012CB821600); 国家自然科学基金(21132001).

Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes

Kunbing Ouyang^a,b, Zhenfeng Xi^b

a Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
b Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China

Received:2014-06-30 Revised:2014-07-21 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Basic Research Program of China (973 Program, 2012CB821600) and the National Natural Science Foundation of China (21132001).

摘要/Abstract

摘要：

由于独特的结构和广泛的应用, 多取代环辛四烯及其苯并稠环衍生物的合成方法研究具有重要意义. 本文报道了一种钯催化烯基溴化物与芳基溴化物的偶联反应. 利用此钯催化的环化自偶联反应, 以中等至较好的收率高选择性地从双溴代芳基或烯基化合物合成了多种二苯并[a,e]环辛四烯衍生物.

关键词: 二溴代化合物, 环辛四烯, 二苯并[a,e]环辛四烯, 1,3-丁二烯, 自偶联反应, 钯催化剂

Abstract:

Cyclooctatetraenes, including dibenzocyclooctatetraenes, are structurally interesting compounds and are widely used in many areas. Therefore, the development of synthetic methods for such compounds has long been attractive. In this work, a Pd-catalyzed coupling reaction between alkenylbromides and arylbromides has been realized. Multi-substituted 1,4-dibromo-1,3-butadienes and o-bromo-2-(2-bromovinyl)benzenes underwent a Pd-catalyzed cyclodimerization reaction to afford the corresponding multi-substituted cyclooctatetraenes and dibenzo[a,e] cyclooctatetraenes, respectively, in high yields and with excellent regioselectivity.

Key words: Dibromide, Cyclooctatetraene, Dibenzo[a,e]cyclooctatetraene, 1,4-Dibromo-1,3-butadiene, Homo-coupling, Palladium catalyst

欧阳昆冰, 席振峰. 钯催化二溴代化合物自偶联环化合成二苯并[a,e]环辛四烯[J]. 催化学报, 2015, 36(1): 24-32.

Kunbing Ouyang, Zhenfeng Xi. Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes[J]. Chinese Journal of Catalysis, 2015, 36(1): 24-32.

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钯催化二溴代化合物自偶联环化合成二苯并[a,e]环辛四烯

Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes

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