40886-63-3Relevant articles and documents
Photochemical Coupling between Halogenoheterocyclic and Heterocyclic Derivatives
D'Agostini, Agnese,D'Auria, Maurizio
, p. 1245 - 1250 (2007/10/02)
The photochemical reaction between 5-iodo-heteroaryl derivatives 1a-d and both 3-heteroaryl allylic alcohols (2a-b) and acetates (3a-b) have been investigated.The presence of an alcoholic function was not compartible with photochemical coupling since compounds 1a-d were photoreduced in the presence of an alcohol.In contrast, the acetates 3a,b gave the expected coupling products.The presence of a weak electron-withdrawing group on the alkene induced an inverted regiochemistry giving only aryl-aryl coupling products.The same behaviour was observed using 2-(3-acetoxyprop-1-ynyl)thiophene 8, in which case only the product deriving from aryl-aryl coupling was again observed.When 2-prop-1-ynylthiophene 11 was used as starting material, the some product resulting from attack on the methyl group 13 was observed.Photochemical coupling between 2-thienylacetonitrile (14) and halogenothienyl derivatives 1b,c gave no reaction product.In contrast, the irradiation of methyl 2-thienylacetate 15 and methyl 2-(2-thienyl)propionate (17) in the presence of 1b,c did give the corresponding coupling products.
