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Cu(OTf)2/NBS-Mediated Tandem Reaction of 1-Cinnamyl Alcohol-o-Carboranes via Ring Opening of Oxetane with Arenes: An Alternative Approach for the Synthesis of C-Alkenyl-o-Carboranes
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.joc.2c01217
Cai-Yan Zhang 1 , Ke Cao 1 , Han-Bo Yang 1 , Li-Fang Ding 1 , Junxiao Yang 1
Affiliation  

The Cu(OTf)2/NBS-mediated tandem reaction of 1-cinnamyl alcohol-o-carboranes for the synthesis of C-alkenyl-o-carboranes has been developed. Mechanism studies demonstrated that the Cu(OTf)2-promoted ring opening of oxetane with electron-rich arenes as soft nucleophiles was involved and was the key step for the transformation. This work provided an alternative strategy for the synthesis of C-alkenyl-o-carboranes, which has an important reference for the synthesis of o-carborane derivatives with diversity.

中文翻译:

Cu(OTf)2/NBS 介导的 1-肉桂醇-邻碳硼烷的串联反应通过氧杂环丁烷与芳烃的开环反应:合成 C-烯基-邻碳硼烷的另一种方法

已经开发了 Cu(OTf) 2 /NBS 介导的 1-肉桂醇-碳硼烷的串联反应,用于合成 C-烯基-碳硼烷。机理研究表明,Cu(OTf) 2促进了以富电子芳烃为软亲核试剂的氧杂环丁烷开环,是转化的关键步骤。该工作为C-烯基邻碳硼烷的合成提供了一种替代策略,对合成具有多样性的碳硼烷衍生物具有重要参考价值。
更新日期:2022-08-03
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