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New Synthesis of Furans: the Rhodium‐Catalysed Carbonylative Addition of Arylboronic Acids to Propargylic Alcohols/ Cyclisation Sequence
Author(s) -
Dheur Julien,
Sauthier Mathieu,
Castanet Yves,
Mortreux André
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900683
Subject(s) - chemistry , rhodium , furan , iodide , catalysis , organic chemistry , sequence (biology) , carbonylation , methyl iodide , reaction conditions , combinatorial chemistry , carbon monoxide , biochemistry
The rhodium‐catalysed carbonylative addition of arylboronic acids to propargylic alcohols yields gamma‐hydroxy enones that are readily cyclised through a dehydration step to the corresponding furan analogues. The transformation was improved thanks to the screening of the reaction conditions and consequent improvements were obtained from the use of dicarbonylrhodium iodide [Rh(CO) 2 I] 2 as catalyst precursor. The generalisation of the reaction was then further investigated by employing variously substituted arylboronic acids and propargylic alcohols.