Al2O3-Supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A Protocol for the Synthesis of Unsymmetrical Diaryl and Alkyl Aryl Selenides
Al2O3-Supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A Protocol for the Synthesis of Unsymmetrical Diaryl and Alkyl Aryl Selenides
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DOI：
10.1021/jo100755g
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发表时间：
2010-07-16
影响因子：
3.6
通讯作者：
Ranu, Brindaban C.
中科院分区：
文献类型：
--
作者：
Bhadra, Sukalyan;Saha, Amit;Ranu, Brindaban C.
氧化铝负载硫酸铜催化溴化苯基硒在有机硼烷、有机硅烷和有机锡烷中的亲电取代反应，为不对称二芳基硒醚和烷基芳基硒醚的合成提供了一条新的有效途径。以高产率合成了一系列芳基、烷基和杂芳基苯基硒醚。该催化剂价格低廉，对生态和用户友好，并且可回收。涉及铜辅助的亲核置换的Br在PhSeBr的温和亲核试剂的机制进行了描述。
Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.