Assessing counterion effects in gold-catalyzed domino spirocyclization: an industrial perspective on hydrogen bonding. Issue 35 (2nd September 2020)

• Record Type: Journal Article
• Authors: Li, Yunhe; Zhao, Xiang
• Is Part Of: Physical chemistry chemical physics. Volume 22:Issue 35(2020)
• Page Start: 19606
• Page End: 19612
• Publication Date: 2020-09-02
• Subjects: Chemistry, Physical and theoretical -- Periodicals; 541.3
• DOI: 10.1039/d0cp03367g
• Languages: English
• ISSNs: 1463-9076

Abstract

Abstract : Different roles of some hydrogen bonding in gold-catalyzed ipso-cyclization to diverse polyheterocyclic frameworks are exposed. The correlation between hydrogen bonding parameters and chemoselectivity is determined. Abstract : We herein report a computational study of the hydrogen bonding in gold-catalyzed ipso -cyclization to diverse polyheterocyclic frameworks. The different roles of these hydrogen bonds are analyzed for the different ipso -cyclization reactions. The fine-tunability of the electronic as well as steric properties of gold counterions contributed substantially to the popularity of the dearomatization reaction, with robust applications in total synthesis and gold catalysis. We have found correlation between the hydrogen bonding parameters and chemoselectivity in gold-catalyzed spirocyclization, playing critical roles in determining the reaction direction of counterion-based enantioselective gold catalysis. The expanded use of counterions via hydrogen bonding interaction can occupy an important role in the future concerning catalyst optimization in gold catalysis.