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Gold(I)‐Catalyzed 1,4‐ and/or 1,5‐Heteroaryl Migration Reactions through Regiocontrolled Cyclizations
Author(s) -
Wang Chengyu,
Xie Xin,
Liu Jun,
Liu Yuanhong,
Li Yuxue
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405190
Subject(s) - regioselectivity , indene , chemistry , catalysis , furan , thiophene , combinatorial chemistry , organic chemistry , medicinal chemistry
Gold(I)‐catalyzed regioselective cycloisomerizations of furan‐ynes have been described. The reaction provides a concise access to stereodefined trisubstituted alkenes by endo cyclization with concomitant 1,5‐migration of the furanyl group in the presence of unactivated 3 Å molecular sieves. In the absence of molecular sieves, indene products are generated by exo cyclization, followed by 1,4‐furanyl migration/cyclization. The scope for 1,5‐migrations can be extended to other heterocycles, such as benzofurans, thiophenes, and pyrroles.