Alumina-Supported Cu(II), A Versatile and Recyclable Catalyst for Regioselective Ring Opening of Aziridines and Epoxides and Subsequent Cyclization to Functionalized 1,4-Benzoxazines and 1,4-Benzodioxanes
Alumina-Supported Cu(II), A Versatile and Recyclable Catalyst for Regioselective Ring Opening of Aziridines and Epoxides and Subsequent Cyclization to Functionalized 1,4-Benzoxazines and 1,4-Benzodioxanes
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DOI：
10.1021/jo101916e
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发表时间：
2010-12-17
影响因子：
3.6
通讯作者：
Ranu, Brindaban C.
中科院分区：
文献类型：
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作者：
Bhadra, Sukalyan;Adak, Laksmikanta;Ranu, Brindaban C.
氧化铝负载铜(II)是一种易于获得的催化剂，它可以高效地催化氮杂环丙烷和环氧化物开环，然后与相应的中间体环合，在一锅中高产率地合成各种官能化的1，4-苯并恶嗪和1，4-苯并二恶烷。氮杂环丙烷和环氧化物的环裂解具有高度的区域选择性。该催化剂价格低廉，对空气不敏感，对环境友好，可回收利用。推测了催化剂的作用和反应途径。该方案被成功地用于在一锅中形成三个碳-杂原子键，即C-O、C-N和C-S键。
An easily accessible catalyst, alumina-supported copper(II), efficiently catalyzes the ring opening of aziridines and epoxides followed by cyclization of the corresponding intermediate to produce a variety of functionalized 1,4-benzoxazines and 1,4-benzodioxanes, respectively, in one pot without any ligand in high yields. The ring cleavages of aziridines and epoxides are highly regioselective. The catalyst is inexpensive, non-air-sensitive, environmentally friendly, and recyclable. The function of the catalyst and the reaction pathway are postulated. This protocol is successfully utilized for the formation of three carbon-heteroatom bonds, namely, C-O, C-N, and C-S, in one pot.