Palladium-Catalyzed Double Reductive Cyclization of 2,3-Dinitro-1,4-dialkenylbenzenes. Synthesis of 1H,8H-Pyrrolo[3,2-g]indoles.

Palladium-Catalyzed Double Reductive Cyclization of 2,3-Dinitro-1,4-dialkenylbenzenes. Synthesis of 1H,8H-Pyrrolo[3,2-g]indoles.
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DOI:
10.1021/acs.joc.9b03290
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发表时间:
2020-03-20
影响因子:
3.6
通讯作者:
Soderberg, Bjorn C. G.
Soderberg, Bjorn C. G.
中科院分区:
化学2区
文献类型:
--
作者:
Ansari, Nurul H.;Banini, Serge;Cummings, Matthew M.;Soderberg, Bjorn C. G.

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发展了一条合成对称和不对称1H,8H-吡咯并[3,2-g]吲哚的灵活路线。关键步骤和最终步骤是双钯催化的一氧化碳催化的1,4-二烯基-2,3-二硝基苯的还原环化反应。通过1,4-二溴-2,3-二硝基苯与烯基锡试剂的双Kosugi-Migita-Stille交叉偶联反应合成了环化前驱体。以4-碘-2,3-二硝基苯基三氟甲磺酸为原料,采用两步交叉偶联法制备了不对称环化前驱体。
A flexible route to both symmetrical and unsymmetrical 1H,8H-pyrrolo[3,2-g]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.
DOI: 10.1021/acs.joc.6b01987
发表时间: 2016-10-07
影响因子: 3.6
作者:
Ansari, Nurul H.;Dacko, Christopher A.;Soderberg, Bjorn C. G.
通讯作者: Soderberg, Bjorn C. G.
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