Premium
Exploring the Versatility of 7‐Alkynylcycloheptatriene Scaffolds Under π‐Acid Catalysis
Author(s) -
Vayer Marie,
Bour Christophe,
Gandon Vincent
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000623
Subject(s) - chemistry , cationic polymerization , catalysis , tandem , reactivity (psychology) , brønsted–lowry acid–base theory , friedel–crafts reaction , aryl , acid catalysis , combinatorial chemistry , organic chemistry , medicine , materials science , alternative medicine , alkyl , pathology , composite material
The reactivity of 7‐alkynycycloheptatrienes tethered to an aryl group under π‐acid catalysis has been studied. A variety of useful cyclic products were synthesized via Au(I)‐catalyzed skeletal reorganization, Cu(II)‐catalyzed hydroarylation, or Brønsted acid‐catalyzed tandem hydroarylation/Friedel‐Crafts reaction. We also report a rare type of skeletal reorganization involving the 1,3‐acetonide tether in the presence of a univalent cationic Ga(I) + complex.