Gold‐Catalyzed Oxidative [2+2+1] Annulations of Aryldiazo Nitriles with Imines To Yield Polyarylated Imidazolium Salts. Issue 18 (30th March 2017)

• Record Type: Journal Article
• Authors: Pawar, Samir Kundlik; Yang, Ming‐Chung; Su, Ming‐Der; Liu, Rai‐Shung
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 18(2017)
• Page Start: 5035
• Page End: 5039
• Publication Date: 2017-03-30
• Subjects: annulations -- arylation -- density functional calculations -- diazo compounds -- gold; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701157
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Gold‐catalyzed oxidative [2+2+1] annulations between two imines and one α‐cyano arylgold carbene afforded polyarylated imidazolium salts and molecular hydrogen efficiently. Control experiments suggest that the gold catalyst alone facilitates the main annulation, whereas Ag + avoids the formation of inactive LAuCN. DFT calculations suggest that the success of this annulation relies on a 6 π‐electrocyclization of cyano‐free intermediates with cis ‐configured imines as initial reagents. Abstract : Five rings for a ring of five : The title reactions between two imines and one α‐cyano arylgold carbene efficiently afford polyarylated imidazolium salts and molecular hydrogen. Density functional calculations suggest that the success of this annulation relies on a 6 π electrocyclization of cyano‐free intermediates with cis ‐configured imines as initial reagents.