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Palladium‐Catalyzed Oxidative Annulation of 1‐Hydroxy‐o‐Carborane with Internal Alkynes: Facile Synthesis of Carborane‐Fused Oxaboroles†
Chinese Journal of Chemistry ( IF 5.4 ) Pub Date : 2020-06-25 , DOI: 10.1002/cjoc.202000307
Ruofei Cheng 1 , Zaozao Qiu 1, 2, 3 , Zuowei Xie 1, 4
Affiliation  

A palladium catalyzed oxidative annulation of 1‐hydroxy‐o‐carborane with internal alkynes via regioselective B(3)—H bond activation has been developed for facile synthesis of a series of C,B‐substituted carborane‐fused oxaboroles. These molecules can undergo intramolecular oxidative dehydrogenative coupling to afford carborane‐fused large π systems for potential applications in organic materials. The reaction mechanism is also proposed, involving hydroxy deprotonation, nucleopalladation of alkyne, regioselective electrophilic B—H substitution and reductive elimination.

中文翻译:

1-羟基-邻-碳硼烷与内部炔烃的钯催化氧化环化:碳硼烷融合的氧杂硼酸酯的简便合成†

已开发了一种通过区域选择性B(3)-H键活化与内部炔烃进行钯催化的1-羟基碳烷的氧化环化反应,以轻松合成一系列C,B取代的碳硼烷稠合的氧杂硼酸。这些分子可以进行分子内氧化脱氢偶联,以提供碳硼烷稠合的大π体系,可用于有机材料中。还提出了反应机理,包括羟基去质子化,炔烃的核palpalpalation,区域选择性亲电B H取代和还原消除。
更新日期:2020-06-25
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