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A Highly Efficient Tandem Reaction of 2‐( gem ‐Dibromovinyl)phenols(thiophenols) with Organosilanes to 2‐Arylbenzofurans (thiophenes)
Author(s) -
Liu Jie,
Chen Wei,
Ji Yong,
Wang Lei
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100875
Subject(s) - chemistry , silanes , tandem , intramolecular force , triphenylphosphine , phenols , ammonium acetate , fluoride , cascade reaction , ammonium fluoride , palladium , organic chemistry , coupling reaction , silylation , catalysis , medicinal chemistry , combinatorial chemistry , silane , inorganic chemistry , materials science , high performance liquid chromatography , composite material
2‐Arylbenzofurans(thiophenes) were prepared through an efficient tandem elimination–intramolecular addition–Hiyama cross‐coupling reaction. In the presence of tetra‐( n ‐butyl)ammonium fluoride (TBAF), palladium(II) acetate [Pd(OAc) 2 ] and triphenylphosphine (PPh 3 ), the reaction of 2‐( gem ‐dibromovinyl)phenols(thiophenols) with phenyl(trialkoxy)silanes proceeded smoothly and generated the corresponding products with good yields in one‐pot. It should be noted that TBAF plays an important role in the tandem reaction.