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Relay‐Heck Cross‐Coupling Between Alkenyl Halides and Unsaturated Alcohols in the Synthesis of Open‐Chain Analogues of Musk Odorant Vulcanolide
Author(s) -
Lenormand Anthony,
Reyes Méndez Lucía,
Coulomb Julien
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101080
Subject(s) - alkene , heck reaction , chemistry , halide , alcohol , palladium , organic chemistry , catalysis , combinatorial chemistry , stereochemistry
Unactivated alkenyl iodides and bromides underwent an unprecedented palladium‐catalyzed relay‐Heck cross‐coupling with a whole range of alkenols of different chain lengths linking the alkene and the alcohol, affording unsaturated aldehydes and ketones in moderate to good yields. In contrast, alkenyl triflates were not suitable partners for this reaction. This method allowed the preparation of open‐chain analogues of the musk odorant Vulcanolide, several of which retained key olfactory properties of the parent molecule.