钯催化的 2,3-二硝基-1,4-二烯基苯的双还原环化反应。1,8-吡咯并[3,2-]吲哚的合成。
Palladium-Catalyzed Double Reductive Cyclization of 2,3-Dinitro-1,4-dialkenylbenzenes. Synthesis of 1,8-Pyrrolo[3,2-]indoles.
机构信息
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States.
出版信息
J Org Chem. 2020 Mar 20;85(6):4002-4010. doi: 10.1021/acs.joc.9b03290. Epub 2020 Mar 6.
Abstract
A flexible route to both symmetrical and unsymmetrical 1,8-pyrrolo[3,2-]indole has been developed. The key and ultimate step is a double palladium-catalyzed, carbon monoxide mediated reductive cyclization of 1,4-dialkenyl-2,3-dinitrobenzenes. The cyclization precursors were prepared by a double Kosugi-Migita-Stille cross coupling of 1,4-dibromo-2,3-dinitrobenzene with an alkenyltin reagent to give symmetrical products. Unsymetrical cyclization precursors were prepared by two sequential cross couplings using 4-iodo-2,3-dinitrophenyl trifluoromethanesulfonate as the starting material.
摘要
已经开发出一种灵活的方法来合成对称和非对称的 1,8-吡咯并[3,2-f]吲哚。关键和最终步骤是双钯催化、一氧化碳介导的 1,4-二烯基-2,3-二硝基苯的还原环化。环化前体通过双 Kosugi-Migita-Stille 交叉偶联 1,4-二溴-2,3-二硝基苯与烯基锡试剂制备得到对称产物。非对称环化前体通过使用 4-碘-2,3-二硝基三氟甲磺酸苯酯作为起始原料的两次连续交叉偶联来制备。
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