Palladium-catalyzed synthesis of 2-allylindole and 2-allylbenzofuran derivatives from 2-((trimethylsilyl)ethynyl)arenes

被引：6
作者：
Chakraborty, Amrita [1 ]
Jyothi, Konanki [1 ]
Sinha, Surajit [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 50期
关键词：
Heterocycles; 2-((Trimethylsilyl)ethynyl)arenes; Palladium catalysis; Regioselective allylation; Stereoselective allylation; O-ALKYNYLTRIFLUOROACETANILIDES; REGIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; POTENT INHIBITORS; INDOLES; ALLYLATION; 3-ALLYLINDOLES; CYCLIZATION; BENZOFURANS; CARBONATES;
D O I：
10.1016/j.tetlet.2014.10.049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new protocol for the synthesis of 2-allylindole and 2-allylbenzofuran derivatives has been developed from readily accessible starting material, 2-((trimethylsilyl)ethynyl)arenes via Pd-catalysis. The presence of trimethylsilyl group in the allkyne is vital for this reaction. Stereoselectivity of 2-allylindole derivatives is controlled by the use of different nitrogen-protecting groups for 2-((trimethylsilyl)ethynyl)aniline. The CO2Me protection gives Z-isomers, whereas acetyl protection gives E-isomers. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6795 / 6798
页数：4
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