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ID 15360
file
creator
Kobayashi, Daisuke
Yamamoto, Yuta
Takehira, Katsuomi
subject
Diynes
Dual hydrophosphination
Rare-earth catalysts
NDC
Chemistry
abstract
Dual intermolecular hydrophosphination of conjugated diynes with 2 equiv of diphenylphosphine was catalyzed by ytterbium complexes, Yb(η2- Ph2CNPh)(hmpa)3 (1) and Yb[N(SiMe3) 2]3(hmpa)2 (2), to give the corresponding 1,4-bis(diphenylphosphinyl)buta-1,3-dienes in high yields after oxidative work-up. Distribution of the four possible stereoisomers sharply depended on substituents of the substrates. (Z,Z)-Isomers were predominantly obtained from the disubstituted diynes, together with minor (Z,E)-isomers. On the other hand, the reaction of the terminal diynes provided major (E,Z) and minor (E,E)-butadienes. 1,4-Di-tert-butylbuta-1,3-diyne was exclusively converted to an allenic compound. Moreover, the dual hydrophosphination using phenyphosphine was also performed with 1 and 2. Thus, the reaction of 2 equiv of aromatic alkynes with PhPH2 and subsequent oxidation gave bis(alkenyl) phosphine oxides in preference of the (Z,Z)-stereoisomers.
journal title
Tetrahedron
volume
Volume 62
issue
Issue 11
start page
2511
end page
2519
date of issued
2006-03
publisher
Elsevier Ltd
issn
0040-4020
ncid
publisher doi
language
eng
nii type
Journal Article
HU type
Journal Articles
DCMI type
text
format
application/pdf
text version
author
rights
Copyright (c) 2005 Elsevier Ltd.
relation is version of URL
http://dx.doi.org/10.1016/j.tet.2005.12.049
department
Graduate School of Engineering