116156-20-8

Upstream product

• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 214491-15-3 (E)-(4-iodobut-1-en-3-yn-1-yl)benzene 
• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 
• 122507-69-1 (E)-styryl-lead triacetate 
• 103-64-0 bromostyrene 
• 1066-54-2 trimethylsilylacetylene 
• 42599-24-6 E-styryl iodide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 63145-23-3 2,3-Dimethyl-5,8-diphenyl-6,7-di<(E)-styryl-1,4-naphthochinon 
• 63145-24-4 2,3,5,8-Tetraphenyl-6,7-di<(E)-styryl>-1,4-naphthochinon 

Relevant academic research and scientific papers

One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)–Copper(I) Iodide–Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction

The low loading combination of the complex [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand-free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single-step procedure. The unsymmetrical diarylalkynes can be obtained through a one-pot two-step approach. The reactions of aryl bromides with 1,4-bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4-diaryl-1,3-diynes in a similar fashion. This route to diarylalkynes and 1,4-diaryl-1,3-diynes is complementary to previously reported synthetic procedures. (Figure presented.).

Stereoselective syntheses of (E)- and (Z)-1-arylalk-3-en-1-ynes and (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes via a one-pot multicomponent coupling reaction

Both 1-arylalk-3-en-1-ynes and alka-1,5-dien-3-ynes have been synthesized under extremely mild reaction conditions in good to high yields via a sequential Suzuki-type and Sonogashira reaction in a one-pot manner. Thus, the protocol involves Cu-mediated cross-coupling reaction of (E)- or (Z)- alkenyldisiamylborane with (trimethylsilyl)ethynyl bromide in the presence of 1M NaOMe and Pd/Cu-catalyzed cross-coupling reaction with aryl or alkenyl iodide in the presence of aqueous n-Bu4NOH. The reaction with aryl iodide is tolerant of a wide variety of functional groups on the aromatic ring and leads to the stereoselective formation of (E)- and (Z)-1-arylalk-3-en-1-ynes. In addition, the reactions with (E)- and (Z)-1-iodoalk-1-enes have accomplished the construction of all possible combinations of geometrical isomers, (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes. Georg Thieme Verlag Stuttgart.

Flash vacuum pyrolysis of 1,6-diphenyl-1,5-hexadien-3-ynes: Tandem diaryldienyne cyclizations to form chrysene

Flash vacuum pyrolysis of 1,6-diphenyl-1,5-hexadien-3-yne at 1000°C and its bromo derivative at 800°C yielded chrysene as the major product through tandem diaryldienyne cyclizations.

Palladium-catalyzed cross-coupling of organolead(IV) triacetates with terminal alkynes

The palladium-catalyzed carbon-carbon bond formation of organolead(IV) triacetates with terminal alkynes was accomplished with Pd2(dba)3·CHCl3 (5mol%) and CuI (10mol%) in the presence of NaOMe (2 equiv.) in MeOH/CH3/

Copper-catalyzed cross-coupling of 1-iodoalkynes with organostannanes

Copper-catalyzed cross-coupling of 1-iodoalkynes with organostannanes was readily achieved in the presence of CuI (10 mol%) in DMF at room temperature for 6 hours by adding 1-iodoalkynes slowly to organostannanes.