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A Metal‐Free Synthesis of 2‐Alkyl(or Aryl) Thiomethyl‐2‐cyclohexenones from Cyclic Morita – Baylis – Hillman Bromides
Author(s) -
Baioui Narjes,
Abidi Ahlem,
Rezgui Farhat
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201600136
Subject(s) - chemistry , alkyl , aryl , transition metal , baylis–hillman reaction , medicinal chemistry , catalysis , organic chemistry , metal
Under mild conditions, an efficient and rapid S ‐allylation of thiols with cyclic Morita – Baylis – Hillman ( MBH ) bromides without the need of a transition‐metal catalyst or an expensive additive is described herein. Treatment of the MBH bromides with various thiols or ethane‐1,2‐dithiol in the presence of Et 3 N regioselectively affords the corresponding 2‐alkyl(or aryl) thiomethyl‐2‐cyclohexenones or the perhydro benzo[1,4]dithiepinone, respectively, in moderate to good yields (40 – 73%). The reaction is rapid and carried out in THF at room temperature.