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Gold‐Catalyzed Hydroarylating Cyclization of 1,2‐Bis(2‐iodoethynyl)benzenes
Author(s) -
Nösel Pascal,
Müller Vanessa,
Mader Steffen,
Moghimi Setareh,
Rudolph Matthias,
Braun Ingo,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400749
Subject(s) - chemistry , aromatization , catalysis , carbenoid , halogen , selectivity , combinatorial chemistry , molecule , photochemistry , organic chemistry , rhodium , alkyl
1,5‐Diynes bearing halogen‐substituted alkynes were synthesized and converted in the presence of a gold catalyst. In contrast to the corresponding hydroarylating aromatization reaction with terminal alkynes, a totally different reaction mode was observed. Instead of the expected dual catalysis pathway, only one gold center is needed and a 1,2‐halogen migration is initiated in which either a gold vinylidene species or a gold carbenoid is involved. By the incorporation of one solvent molecule, diiodinated aromatic products are obtained in high selectivity.