79756-95-9

Upstream product

• 917-92-0 3,3-Dimethylbut-1-yne 
• 98-59-9 p-toluenesulfonyl chloride 
• 766-97-2 4-n-methylphenylacetylene 
• 65114-80-9 1-(4-Methylphenyl)-1,1-dichlorethan 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 
• 1401205-59-1 Pd(triflate )Me(p-tolyl)(C≡CBu^t)(1,2-bis-(dimethylphosphino)ethane) 
• 1401205-60-4 Pd(triflate )Me(p-tolyl)(C≡CBu^t)(2,2′-bipyridine) 
• 1401205-61-5 Pd(triflate )Me(p-tolyl)(C≡CBu^t)(1,10-phenanthroline) 
• 75-98-9 Trimethylacetic acid 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 51350-44-8 1-((4 methylphenyl)diazenyl)morpholine 
• 106-49-0 p-toluidine 

Downstream Products

• 1397283-43-0 (Z)-2-(3,3-dimethyl-1-(p-tolyl)but-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 142039-30-3 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methylbenzene 
• 1144426-66-3 (Z)-1-(3,3-dimethylbut-1-en-1-yl)-4-methylbenzene 

Relevant academic research and scientific papers

Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp2)-C(sp) Bond Formation

An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or commercially available organotrifluoroborate salts.

1-Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium-ILs, with [BMIM(SO3H)][OTf] or Sc(OTf)3 as Promoter, and Pd(OAc)2 or NiCl2·glyme as Catalyst

1-Aryltriazenes, the protected and more stable form of aryl-diazonium species, can be conveniently unmasked with Br?nsted acidic-IL or Sc(OTf)3 and coupled with a host of aryl/heteroaryl boronic acids, styrenes, and aryl/alkyl acetylenes in the Suzuki, Heck and Sonogashira reactions in one-pot and in respectable isolated yields, by using palladium or nickel catalyst in readily available imidazolium ILs as solvent, under mild conditions. The scope of these reactions are explored, and the potential for recovery/reuse of the IL solvent is also addressed.

Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes

A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.

Selective Carbonyl?C(sp3) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis

Carbon–carbon bond cleavage/functionalization is synthetically valuable, and selective carbonyl?C(sp3) bond cleavage/alkynylation presents a new perspective in constructing ynamides, ynoates, and ynones. Reported here is the first alkoxyl-radical-enabled carbonyl?C(sp3) bond cleavage/alkynylation reaction by photoredox catalysis. The use of novel cyclic iodine(III) reagents are essential for β-carbonyl alkoxyl radical generation from β-carbonyl alcohols, including alcohols with high redox potential (EoxP>2.2 V vs. SCE in MeCN). β-Amide, β-ester, and β-ketone alcohols yield ynamides, ynoates, and ynones, respectively, for the first time, with excellent regio- and chemoselectivity under mild reaction conditions.

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.

A Simple and Efficient Palladium Catalyst of Nitrogen-Based Ligand for Cu(I)- and Amine-Free Sonogashira Reaction

Glycine, as a kind of commercially available and inexpensive ligand, is used to prepare an air-stable and water-soluble catalyst used in Sonogashira reaction in our study. In the presence of 1% [PdCl2(NH2CH2COOH)2/su

Synthetic and computational studies of the palladium(iv) system Pd(alkyl)(aryl)(alkynyl)(bidentate)(triflate) exhibiting selectivity in C-C reductive elimination

Synthetic routes to methyl(aryl)alkynylpalladium(iv) motifs are presented, together with studies of selectivity in carbon-carbon coupling by reductive elimination from PdIV centres. The iodonium reagents IPh(CCR)(OTf) (R = SiMe3, Bu

Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions

Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)2 and Ag2O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis of 1H-isochromenes and diynes. It is noteworthy that the reaction proceeds under ligand-free and relative lower loading Pd conditions, and the maximal TONs (turnover numbers) of the reaction are up to 720,000.

Iron/copper-catalyzed C-C cross-coupling of aryl iodides with terminal alkynes

Synergic effect of iron and copper salts as catalysts for the Sonogashira-Hagihara cross-couplings of aryl iodides with terminal alkynes is demonstrated. High yields of cross-coupled products are obtained under conditions that are smoother than those using only CuI as catalyst. Furthermore no expensive or/and toxic ligand is required.

Palladium-catalyzed desulfitative Sonogashira-Hagihara cross-couplings of arenesulfonyl chlorides and terminal alkynes

For the first time, conditions have been found for the palladium-catalyzed desulfitative carbon-carbon cross-coupling of arenesulfonyl chlorides with aryl- and alkylacetylenes. Pd2(dba)3/P(t-Bu)3 and CuI provide the best c