4980-70-5

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 72705-83-0 4-benzyl-3-phenylisoxazol-5(4H)-one 
• 93321-44-9 1,3-diphenylprop-2-yn-1-yl acetate 
• 79965-53-0 C₂₉H₂₂ 
• 536-74-3 phenylacetylene 
• 29127-97-7 2-Tosylazo-1,3-diphenylpropen 
• 5171-98-2 Diphenylacetone hydrazone 
• 100-39-0 benzyl bromide 
• 72568-87-7 C₂₁H₁₈O₂S 
• 100-52-7 benzaldehyde 
• 111976-52-4 (1-Benzenesulfonyl-2-phenyl-ethyl)-trimethyl-silane 
• 673-32-5 1-Phenylprop-1-yne 
• 591-50-4 iodobenzene 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 

Downstream Products

• 3780-00-5 (R)-1,3-diphenylallene 
• 23464-17-7 1,3-diphenylpropane-1,2-dione 
• 1083-30-3 dihydrochalcone 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 35030-49-0 Methyl 2,3-diphenylpropanoate 
• 13988-68-6 (α-Chlor-cis-styryl)-phenyl-cyclopropenon 
• 13894-05-8 1-Phenyl-2-(α-chlor-styryl)-cyclopropenon-(3) 
• 56813-85-5 (E)-1-Bromo-1,3-diphenyl-1-propen 
• 19753-97-0 phenyl-1 dibenzyl-2,3 naphtalene 
• 3780-00-5 1-(3-phenyl-1,2-propadienyl)benzene 
• 61507-95-7 1-Chloro-1,3-diphenyl-2-(phenylmethyl)propene 
• 19784-92-0 1,3-diphenyl-2,3-dihydro-1H-indene 
• 15972-53-9 acide benzylidene-3 phenyl-2 cyclopropanecarboxylique (1R^*,2R^*) E 
• 15972-53-9 acide benzylidene-3 phenyl-2 cyclopropanecarboxylique (1R^*,2R^*) Z 

Relevant academic research and scientific papers

Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes

Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de

Fast heck-cassar-sonogashira (hcs) reactions in green solvents

The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

A Copper-Catalyzed Sonogashira Coupling Reaction of Diverse Activated Alkyl Halides with Terminal Alkynes Under Ambient Conditions

We describe a copper-catalyzed Sonogashira coupling reaction of alkyl halides with terminal alkynes under ambient conditions, efficiently providing a versatile tool for the construction of substituted alkynes. A new proline-based N,N,P-ligand is utilized to promote the transformation under a mild reaction condition. Diverse alkyl halides, such as primary and secondary (hetero)benzyl chlorides and bromides, secondary and tertiary α-bromo amides and propargylic bromide, are applicable to provide a wide array of alkynes. (Figure presented.).

Compound containing carbon-silicon bond and application thereof

The invention discloses a compound containing a carbon-silicon bond and application of the compound in construction of the carbon-carbon bond. The invention provides an application of a compound containing the carbon-silicon bond as shown in a formula I or a formula I' in a chemical reaction for constructing the carbon-carbon bond, wherein one carbon in the carbon-carbon bond is from carbon connected with silicon in the compound containing the carbon-silicon bond. According to the preparation method, the compound containing the carbon-silicon bond is used for providing a carbon free radical, and the carbon free radical can directly react with carbon provided in another molecule under a mild condition to construct the carbon-carbon bond; the preparation method is wider in substrate application range, is suitable for functional group activated C and carbon free radical substrates, and is also suitable for unactivated C-H bond substrates.

Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents

An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).

The Direct Conversion of α-Hydroxyketones to Alkynes

Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.

Conjugated mesoporous polyazobenzene–Pd(II) composite: A potential catalyst for visible-light-induced Sonogashira coupling

We herein report the direct harnessing of visible light energy by a novel semiconducting azobenzene-based colloidal porous organic polymer, B3-Azo4 amenable to post-synthetic Pd(II)-complexation for photo-induced Sonogashira coupling using polymer → metal energy transfer process. Completely mesoporous nano-sized particles of the obtained organic network manifested excellent Pd(II) coordinating ability and afforded desired catalytic products at room temperature under aerobic condition in aqueous medium. The protocol remained valid for different aromatic and aliphatic substrates as well. A possible reaction mechanism for photo-mediated Sonogashira coupling catalyzed by Pd-B3-Azo4 is also proposed.

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)-C(sp) bond formation catalyzed by a B12 complex

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported. The robust B12 catalyst and Ir photocatalyst provided high turnover numbers of over 33?000 for the reactions.

Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis

A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination. (Figure presented.).