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A synthesis of deuterated methyleugenol via transition metal‐catalyzed coupling of substituted deuterated benzyl chloride with vinylmagnesium bromide
Author(s) -
Bouges Hélène,
Antoniotti Sylvain
Publication year - 2017
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3374
Subject(s) - chemistry , bromide , deuterium , catalysis , magnesium bromide , medicinal chemistry , chloride , transition metal , metal , magnesium , organic chemistry , physics , quantum mechanics
Methyleugenol monodeuterated on the benzylic position, 4‐(1‐deuteroprop‐2‐enyl)‐1,2‐dimethoxybenzene, was synthesised in > 87% isotopic enrichment and in three steps from veratraldehyde. Key steps involved the reduction of veratraldehyde by LiAlD 4 to install a single deuterium atom at the benzylic position and a Pd‐ or Ni‐catalyzed coupling of the corresponding monodeuterobenzyl chloride with vinyl magnesium bromide.