Gold‐Catalyzed Hydroarylating Cyclization of 1, 2‐Bis(2‐iodoethynyl)benzenes. Issue 2 (29th December 2014)

• Record Type: Journal Article
• Authors: Nösel, Pascal; Müller, Vanessa; Mader, Steffen; Moghimi, Setareh; Rudolph, Matthias; Braun, Ingo; Rominger, Frank; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 2/3(2015)
• Page Start: 500
• Page End: 506
• Publication Date: 2014-12-29
• Subjects: gold catalysis -- gold vinylidenes -- 1, 2‐halogen migration -- iodoalkynes -- naphthalenes; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400749
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :