Efficient preparation of 2-azulenylboronate and Miyaura-Suzuki cross-coupling reaction with aryl bromides for easy access to poly(2-azulenyl)benzenes
作者:Shunji Ito、Tomomi Terazono、Takahiro Kubo、Tetsuo Okujima、Noboru Morita、Toshihiro Murafuji、Yoshikazu Sugihara、Kunihide Fujimori、Jun Kawakami、Akio Tajiri
DOI:10.1016/j.tet.2004.04.057
日期:2004.6
describes an efficient preparation of 2-azulenylboronate (6) starting from 2-iodoazulene by halogen–metal exchange reaction using n-BuLi and subsequent quenching with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The boronate 6 has been found to undergo Pd-catalyzed Miyaura-Suzuki cross-coupling reaction with a range of aryl bromides including aromatic poly bromides utilizing Pd2(dba)3–P(t-Bu)3
本文介绍了一种高效的制备2-氮杂氮硼烷(6)的方法,该方法由2-碘杂氮杂苯通过卤素-金属交换反应使用n -BuLi进行反应,然后用2-异丙氧基-4,4,5,5-四甲基-1,3淬灭, 2-二氧杂硼烷。已发现硼酸酯6与Pd 2(dba)3 -P(t -Bu)3进行的Pd催化的Miyaura-Suzuki交联反应与一系列芳基溴化物包括芳族多溴化物作为催化剂,并建立了生产新型聚(2-氮杂烯基)苯的策略,然而,发现其中的一些不溶于普通的有机溶剂。通过循环伏安法(CV)检查了2-芳基azulenes和聚(2-azulenyl)苯的氧化还原行为,并将其与先前报道的6-azulenyl苯衍生物的氧化还原行为进行了比较。