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Cationic Rhodium(I)‐Catalyzed Carbonylative [2+2+1] Cycloaddition of Diynes
Author(s) -
Morimoto Tsumoru,
Jia JingWen,
Yamaguchi Yoshiko,
Tanimoto Hiroki,
Kakiuchi Kiyomi
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000436
Subject(s) - rhodium , chemistry , cationic polymerization , catalysis , cycloaddition , carbonylation , medicinal chemistry , organic chemistry , carbon monoxide
We describe Rh(I)‐catalyzed carbonylative [2+2+1] cycloaddition reactions of diynes with CO to give cyclopentadienone derivatives (CPDs). Previous reports on the use of neutral rhodium(I) complexes, such as [RhCl(cod)] 2 and RhCl(PPh 3 ) 3 , indicate that no CPD products are formed or that they are produced in low yields, even at elevated temperatures. The reaction described herein, which uses a cationic rhodium(I) complex, [Rh(cod) 2 ]BF 4 , as a catalyst, proceeds smoothly at room temperature to give cyclopentadienone derivatives. The key to this is the use the cationic rhodium(I) complex as a catalyst, which produces an additional coordination site on the rhodium for the substrate (a diyne) to approach, than neutral rhodium complexes.