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Copper‐catalyzed C(sp 2 )–C(sp) Sonogashira‐type cross‐coupling reactions accelerated by polycyclic aromatic hydrocarbons
Author(s) -
Xu Wei,
Yu Bo,
Sun Huaming,
Zhang Guofang,
Zhang Weiqiang,
Gao Ziwei
Publication year - 2015
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3298
Subject(s) - chemistry , sonogashira coupling , phenylacetylene , catalysis , pyrene , aryl , copper , hydrocarbon , polycyclic aromatic hydrocarbon , aromatic hydrocarbon , substrate (aquarium) , organic chemistry , alkyne , combinatorial chemistry , polymer chemistry , medicinal chemistry , palladium , alkyl , oceanography , geology
Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf) 2 /pyrene system was subsequently employed to synthesize phenylacetylene‐based fluorescent compounds. Copyright © 2015 John Wiley & Sons, Ltd.