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One‐Pot Process to Carborano‐Coumarin via Catalytic CascadeDehydrogenative Cross‐Coupling
Chinese Journal of Chemistry ( IF 5.4 ) Pub Date : 2020-02-22 , DOI: 10.1002/cjoc.201900475
Yik Ki Au 1 , Hairong Lyu 1 , Yangjian Quan 1 , Zuowei Xie 1
Affiliation  

Ir‐catalyzed cascade dehydrogenative CH/BH and BH/OH cross‐coupling of carboranyl carboxylic acid with readily available benzoic acid has been achieved, leading to the facile synthesis of previously unavailable carborano‐coumarin in a simple one‐pot process. Two cage B—H, one aryl C—H and one O—H bonds are activated to construct efficiently new B—C and B—O bonds. The cascade cyclization can stop at the first B—H/C—H cross‐coupling step by tuning the reaction conditions, resulting in a series of α‐carboranyl benzoic acid and aryl carborane derivatives. Control experiments indicate that B—H/C—H dehydrocoupling proceeds preferentially over B—H/O—H dehydrocoupling, and both directing groups and oxidants are crucial for this reaction. An iridium(V) intermediate is proposed to be involved in the catalytic cycle.

中文翻译:

通过催化级联反应一氧化碳法制取Carborano-Coumarin的过程

碳硼烷羧酸与现成的苯甲酸的Ir催化级联脱氢CH / BH和BH / OH交联已实现,从而可以通过简单的一锅法轻松合成先前无法获得的碳硼烷-香豆素。激活两个笼型B-H,一个芳基C-H和一个O-H键,以有效地构建新的B-C和B-O键。通过调节反应条件,级联环化可以在第一个B / H / C-H交叉偶联步骤中停止,从而产生一系列α-碳硼烷基苯甲酸和芳基碳硼烷衍生物。对照实验表明,B / H / CH脱氢偶联反应比B / H / OH脱氢偶联反应优先进行,并且导向基团和氧化剂都对该反应至关重要。提出了铱(V)中间体参与催化循环。
更新日期:2020-02-23
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