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Ruthenium‐Catalyzed One‐Pot Synthesis of ( E )‐(2‐Arylvinyl)boronates through an Isomerization/Cross‐Metathesis Sequence from Allyl‐Substituted Aromatics
Author(s) -
Hemelaere Rémy,
Caijo Frédéric,
Mauduit Marc,
Carreaux François,
Carboni Bertrand
Publication year - 2014
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.201402192
Subject(s) - isomerization , chemistry , ruthenium , metathesis , catalysis , sequence (biology) , organic chemistry , combinatorial chemistry , transformation (genetics) , polymerization , gene , biochemistry , polymer
We described the efficient preparation of ( E )‐(2‐arylvinyl)boronates from allylbenzene derivatives on the basis of an isomerization/cross‐metathesis sequence catalyzed by a modified Hoveyda–Grubbs catalyst. The implementation of the experimental procedure was simple and compatible with a large variety of substrates. This methodology provides a new chemical transformation not described to date. Allyl‐substituted aromatics can thus be converted into diversely functionalized compounds, such as ( E )‐stilbene derivatives or ( E )‐vinyl azides, in only two steps.