An efficient palladium-catalysed coupling of terminal alkynes with aryl halides under Jeffery's conditions

N-substituted-1,2,3-triazoles: synthesis, characterization and evaluation as cannabinoid ligands

“…24 This procedure was convenient regarding the safety issues using tri-n-butyltin azide compared to the highly explosive hydrazoic acid. The tributylstannyl group could be subsequently replaced by a proton under mild conditions.…”

“…Hz, C-1'), 56.9 (CH 2 ), 47.8 (C-1"), 32.3 (C-2"), 25.1 (C-4"), 24.4 (C-3") ppm. ESI-MS: m/z (%) = 382 (27), 380 (27) …”

A copper-free Sonogashira reaction using nickel ferrite as catalyst in water

“…The presence of Cu/O 2 in the reaction media can cause to a side reaction of Glaser-type dimerization of acetylene substrates to afford diyne [2,15] as well as contamination of the products with poisonous metal residues [16]. This is one of the main drawbacks of the Sonogashira reaction that has been partially solved employing copper-free reactions [17,18]. Most catalytic systems used for the Sonogashira reaction are homogeneous palladium-based catalysts having tedious recovery, if not impossible [19].…”

“…Although active alkyl halides were successfully coupled with phenylacetylene (entries [16][17][18], the yields of the reaction of inactive alkyl halides were not high enough (entries [19][20][21][22].…”

Studies toward the Synthesis of (−)‐Zampanolide: Preparation of the Macrocyclic Core

“…In an attempt to accelerate the reaction and increase the conversion, use of tetrabutylammonium iodide (TBAI) as an additive 50 was investigated (entries 5–8). Quaternary ammonium salts have been employed to accelerate metal-mediated couplings involving alkynes, 51 alkenes, 52 and alkyl 53 substrates. When TBAI was employed for the coupling of acetate 28 and model vinyl stannane 7 , the reaction proceed to completion and provided the 1,3-diene product 30 as the sole product.…”