A Cleavage‐Modification‐Reassembly Process Catalyzed by Rhodium and Brønsted Acid for the Synthesis of Multi‐Substituted Anilines. Issue 10 (3rd April 2020)

• Record Type: Journal Article
• Authors: Liu, Xiangrong; Xiao, Guolan; Xu, Xinfang; Kang, Zhenghui; Zhang, Dan; Hu, Wenhao
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 10(2020)
• Page Start: 1961
• Page End: 1965
• Publication Date: 2020-04-03
• Subjects: Metal carbene -- Diazo compound -- Ylide -- Quinone imine ketals -- Synergistic catalysis -- Atom economy; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000193
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A synergistic rhodium‐ and Brønsted acid‐ catalyzed reaction of quinone imine ketals with diazo compounds to access multi‐substituted anilines is presented here. This reaction takes place through a process involving C−O bond cleavage, modification of the leaving alcoholic fragment, and selective reassembly of the reactive fragments. Moderate enantioselectivities are achieved when a chiral 1, 1'‐bi(2‐naphthol)‐based phosphoric acid is used. Abstract :