TY - JOUR
T1 - Palladium-catalyzed trimerizations of terminal arylalkynes
T2 - Synthesis of 1,3-diaryl-2-arylethynyl-1,3-butadienes
AU - Wu, Yao Ting
AU - Lin, Wei Chih
AU - Liu, Chia Ju
AU - Wu, Chuan Yi
PY - 2008/8/4
Y1 - 2008/8/4
N2 - Various 1,3-diaryl-2-arylethynyl-1,3-butadienes 7 have been prepared by the Pd-catalyzed trimerization of arylalkynes 4. Their structures and stereochemistry have been confirmed by X-ray crystal analyses. This procedure provides high regioselectivity to generate adducts Z-7 in moderate to excellent yields. The scope, limitations and regioselectivity of this reaction have been investigated. In DMSO at 180 °C, 1,3-di(1-naphthalenyl)-2-(1- naphthalenylethynyl)-1,3-butadiene (7m) underwent 6π-electrocyclization to form 2-(1-naphthalenyl)-3-(1-naphthalenyl-ethynyl)-1,2-dihydrophenanthrene (21). Under acidic conditions, (1Z)-1,3-diphenyl-2-(1-phenylethynyl)-1,3-butadiene (Z-7a) was converted to 1-methyl-3-phenyl-2-(2-phenyl-1-ethionyl)-2-indene (22) in 75% yield.
AB - Various 1,3-diaryl-2-arylethynyl-1,3-butadienes 7 have been prepared by the Pd-catalyzed trimerization of arylalkynes 4. Their structures and stereochemistry have been confirmed by X-ray crystal analyses. This procedure provides high regioselectivity to generate adducts Z-7 in moderate to excellent yields. The scope, limitations and regioselectivity of this reaction have been investigated. In DMSO at 180 °C, 1,3-di(1-naphthalenyl)-2-(1- naphthalenylethynyl)-1,3-butadiene (7m) underwent 6π-electrocyclization to form 2-(1-naphthalenyl)-3-(1-naphthalenyl-ethynyl)-1,2-dihydrophenanthrene (21). Under acidic conditions, (1Z)-1,3-diphenyl-2-(1-phenylethynyl)-1,3-butadiene (Z-7a) was converted to 1-methyl-3-phenyl-2-(2-phenyl-1-ethionyl)-2-indene (22) in 75% yield.
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U2 - 10.1002/adsc.200800182
DO - 10.1002/adsc.200800182
M3 - Article
AN - SCOPUS:53849090290
VL - 350
SP - 1841
EP - 1849
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 11-12
ER -