Synthesis of tricyclic heterocycles via a tandem aryl alkylation/heck coupling sequence

被引:42
作者
Alberico, Dino [1 ]
Rudolph, Alena [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/jo0617868
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.
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页码:775 / 781
页数:7
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