134752-30-0Relevant academic research and scientific papers
Single electron transfer-induced coupling of alkynylzinc reagents with aryl and alkenyl iodides
Okura, Keisho,Kawashima, Hitomi,Tamakuni, Fumiko,Nishida, Naoya,Shirakawa, Eiji
, p. 14019 - 14022 (2016)
Alkynylzinc reagents were found to undergo coupling with aryl and alkenyl iodides to give arylalkynes and alkenylalkynes without the aid of transition metals. The coupling reaction proceeds through a single electron transfer mechanism, where a substoichiometric amount of a phosphine works as an indispensable activator.
Dual gold/photoredox-catalyzed C(sp)-H arylation of terminal alkynes with diazonium salts
Tlahuext-Aca, Adrian,Hopkinson, Matthew N.,Sahoo, Basudev,Glorius, Frank
, p. 89 - 93 (2015/12/30)
The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described. Using aryldiazonium salts as readily available aryl sources, a range of diversely-functionalized arylalkynes could be synthesized under mild, base-free reaction conditions using visible light from simple household sources or even sunlight. This process, which exhibits a broad scope and functional group tolerance, expands the range of transformations amenable to dual gold/photoredox catalysis to those involving C-H bond functionalization and demonstrates the potential of this concept to access AuI/AuIII redox chemistry under mild, redox-neutral conditions.
Pd- and Ni-catalyzed cross-coupling reactions of functionalized organozinc reagents with unsaturated thioethers
Melzig, Laurin,Metzger, Albrecht,Knochel, Paul
, p. 2948 - 2956 (2011/04/16)
A variety of unsaturated thioethers have been subjected to cross-coupling reactions with functionalized zinc reagents in the presence of a transition-metal catalyst. Three different catalytic systems based on Pd(OAc)2 or [Ni(acac)2] and the ligands S-Phos or DPE-Phos gave the best results. N-Heterocyclic thioethers based on a pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzothiazole, benzoxazole, pyrrole, or quinazoline ring, as well as thiomethylacetylenes, serve as electrophiles in this cross-coupling reaction. Aryl-, heteroaryl-, benzylic, and alkylzinc halides with sensitive functionalities, such as ester, nitrile, or ketone groups react at ambient temperature with unsaturated thioethers using a Ni catalyst. The corresponding Pd-catalyzed reactions require slightly higher temperatures. Large-scale cross-coupling experiments (10-20 mmol) with N-heterocycles are also reported.
