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Copper-Catalyzed Tandem Cross-Coupling/Thermally Promoted [2 + 2] Cycloaddition of 1,6-Enynes and Diazo Compounds To Assemble Methylenecyclobutane-Fused Ring System
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-03-05 , DOI: 10.1021/acs.joc.1c00104 Nuan Chen 1 , Ting Zhou 1 , Hong Zhang 1 , Yuqi Zhu 1 , Ming Lang 1 , Jian Wang 1, 2 , Shiyong Peng 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-03-05 , DOI: 10.1021/acs.joc.1c00104 Nuan Chen 1 , Ting Zhou 1 , Hong Zhang 1 , Yuqi Zhu 1 , Ming Lang 1 , Jian Wang 1, 2 , Shiyong Peng 1
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An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported. A library of methylenecyclobutane-fused ring systems including cyclobuta[b]indolines, cyclobuta[b]benzofuran, benzo[b]cyclobuta[d]thiophene, and bicyclo[3.2.0] structures were obtained in moderate to excellent yields under very mild reaction conditions. The reaction exhibited high proximal-regioselectivity and diastereoselectivity. Moreover, 1,6-allenene has proven to be the key intermediate and proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
中文翻译：
铜催化串联交叉偶联/热促进[2 + 2]的1,6-炔烃和重氮化合物的环加成反应，以组装亚甲基环丁烷-熔融环系统
据报道，通过交叉偶联/ [2 + 2]环加成序列，铜催化的重氮化合物与重氮化合物发生了空前的串联反应。在非常温和的反应下，以中等至极好的收率获得了包括环丁二烯[ b ]二氢吲哚，环丁丁[ b ]苯并呋喃，苯并[ b ]环丁丁[ d ]噻吩和双环[3.2.0]结构的亚甲基环丁烷稠合环系统的库。条件。该反应表现出高的近端区域选择性和非对映选择性。此外，已证明1，6-丙烯是关键中间体，并在不存在铜催化剂的情况下通过热促进的[2 + 2]环加成反应而进行。
更新日期：2021-03-19
中文翻译：
铜催化串联交叉偶联/热促进[2 + 2]的1,6-炔烃和重氮化合物的环加成反应，以组装亚甲基环丁烷-熔融环系统
据报道，通过交叉偶联/ [2 + 2]环加成序列，铜催化的重氮化合物与重氮化合物发生了空前的串联反应。在非常温和的反应下，以中等至极好的收率获得了包括环丁二烯[ b ]二氢吲哚，环丁丁[ b ]苯并呋喃，苯并[ b ]环丁丁[ d ]噻吩和双环[3.2.0]结构的亚甲基环丁烷稠合环系统的库。条件。该反应表现出高的近端区域选择性和非对映选择性。此外，已证明1，6-丙烯是关键中间体，并在不存在铜催化剂的情况下通过热促进的[2 + 2]环加成反应而进行。
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