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Wittig‐Type Olefination of Alcohols Promoted by Nickel Nanoparticles: Synthesis of Polymethoxylated and Polyhydroxylated Stilbenes
Author(s) -
Alonso Francisco,
Riente Paola,
Yus Miguel
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900951
Subject(s) - chemistry , wittig reaction , phosphonium , nickel , lithium (medication) , nanoparticle , organic chemistry , nanotechnology , medicine , materials science , endocrinology
Nickel nanoparticles were found to promote the Wittig‐type olefination of primary alcohols with phosphorus ylides. The latter can be prepared from the corresponding phosphonium salts with n BuLi or in situ generated with lithium metal. The methodology is especially efficient for the synthesis of stilbenes and is applied in the absence of any additive as ahydrogen acceptor. A new approach to the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol, DMU‐212 and analogues, is presented.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)