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Orthogonal Selectivity in C–H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution
ACS Catalysis ( IF 11.3 ) Pub Date : 2019-09-25 , DOI: 10.1021/acscatal.9b03019
Soumitra Agasti 1 , Bhaskar Mondal 2 , Tapas Kumar Achar 1 , Soumya Kumar Sinha 1 , Anjana Sarala Suseelan 1 , Kalman J. Szabo 3 , Franziska Schoenebeck 2 , Debabrata Maiti 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2019-09-25 , DOI: 10.1021/acscatal.9b03019
Soumitra Agasti 1 , Bhaskar Mondal 2 , Tapas Kumar Achar 1 , Soumya Kumar Sinha 1 , Anjana Sarala Suseelan 1 , Kalman J. Szabo 3 , Franziska Schoenebeck 2 , Debabrata Maiti 1
Affiliation
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Oxidative coupling is a useful tool to synthesize vinylarenes. Despite remarkable successes in linear vinylarene, branched vinylarene synthesis has remained underdeveloped. Overcoming this limitation, herein, we report a chelation-assisted oxidative coupling to generate branched olefinated product in high yield. Exclusive branched selectivity was obtained using alkenyl carboxylic acid. Detailed experimental studies combined with computational investigations suggest that β-migratory insertion, followed by a decarboxylation pathway is operative for the overall transformation.
中文翻译:
C–H烯烃化中的正交选择性:具有未活化脂肪族取代的支链乙烯基芳烃的合成
氧化偶联是合成乙烯基芳烃的有用工具。尽管在线性乙烯基芳烃方面取得了显著成就,但支链乙烯基芳烃的合成仍不发达。克服此限制,在本文中,我们报道了螯合辅助的氧化偶联以高产率产生支化的烯烃化产物。使用链烯基羧酸获得排他性的选择性。详细的实验研究与计算研究相结合表明,β迁移插入,然后通过脱羧途径可用于整体转化。
更新日期:2019-09-26
中文翻译:
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C–H烯烃化中的正交选择性:具有未活化脂肪族取代的支链乙烯基芳烃的合成
氧化偶联是合成乙烯基芳烃的有用工具。尽管在线性乙烯基芳烃方面取得了显著成就,但支链乙烯基芳烃的合成仍不发达。克服此限制,在本文中,我们报道了螯合辅助的氧化偶联以高产率产生支化的烯烃化产物。使用链烯基羧酸获得排他性的选择性。详细的实验研究与计算研究相结合表明,β迁移插入,然后通过脱羧途径可用于整体转化。