Highly efficient and selective synthesis of conjugated triynes and higher oligoynes of biological and materials chemical interest via palladium-catalyzed alkynyl-alkenyl coupling.
Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH=CHCl followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri- , tetra- , and pentaynes. Both display unprecedented high efficiency and selectivity. [reaction: see text]
Métay
Estelle
E
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA.
Hu
Qian
Q
Negishi
Ei-ichi
E
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D010165:Palladium