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Highly Efficient Synthesis of Multisubstituted Furans through Cupric Halide‐Mediated Intramolecular Halocyclization of 1‐(1‐Alkynyl)cyclopropyl Ketones
Author(s) -
Zhu Mei,
Fu WeiJun,
Xu Chen,
Zou GuangLong,
Wang ZhiQiang,
Ji BaoMing
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200601
Subject(s) - chemistry , regioselectivity , halide , intramolecular force , medicinal chemistry , stereoselectivity , cascade , reaction conditions , cascade reaction , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , chromatography
A convenient and efficient method for the synthesis of 3‐halofurans was developed by using a cascade reaction between 1‐(1‐alkynyl)cyclopropyl ketones and cupric halide. Under mild reaction conditions, both 3‐chloro‐ and 3‐bromofuran derivatives were obtained in high yields. The reaction involves consecutive multiple bond formations, includingC–O and C–Br bonds, with high regioselectivity. Mechanistic aspects are described.