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Regio‐ and Stereoselective Dimerization of Arylacetylenes and Optical and Electrochemical Studies of ( E )‐1,3‐Enynes
Author(s) -
Morozov Oleg S.,
Asachenko Andrey F.,
Antonov Denis V.,
Kochurov Vitaly S.,
Paraschuk Dmitry Yu.,
Nechaev Mikhail S.
Publication year - 2014
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.201400062
Subject(s) - chemistry , heptane , carbene , stereoselectivity , stereospecificity , photoluminescence , stereochemistry , electrochemistry , medicinal chemistry , organic chemistry , catalysis , physics , optoelectronics , electrode
The N‐heterocyclic carbene palladium complex (SIPr)Pd(cinnamyl)Cl [SIPr= N , N′ ‐bis(2,4,6‐trimethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene) promotes regio‐ and stereospecific dimerization of a variety of arylalkynes to give ( E )‐1,3‐enynes in good to excellent yields. An efficient and practical procedure for their synthesis was developed using a biphasic aqueous alkali/heptane system. Optical and electronic properties of ( E )‐1,3‐enynes are highly tunable. Depending on the nature of the substituents, HOMO energies vary in the range 5.3–6.0 eV. ( E )‐1,3‐Enynes can exhibit intense photoluminescence in the spectral region 350–500 nm.