77295-68-2

Upstream product

• 558-13-4 carbon tetrabromide 
• 42546-17-8 isophthalic aldehyde dihydrazone 
• 626-19-7 Isophthalaldehyde 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1224169-19-0 1,3-bis[(4-fluorophenyl)ethynyl]benzene 
• 13141-36-1 1,3-bis(phenylethynyl)benzene 
• 1429762-96-8 C₅₈H₅₀O₄P₄ 

Relevant academic research and scientific papers

Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles

We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α-imino gold carbenes by N?S cleavage of sulfilimines. These gold carbenes undergo C?H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3-azabicyclo[3.1.0]hexan-2-imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold-catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza-heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α-imino gold carbenes. Moreover, an unexpected synthesis of 4-acylquinolines (3 examples) from 2-acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2-hydride shift onto the α-imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered.

N-Pyridinyl Sulfilimines as a Source for α-Imino Gold Carbenes: Access to 2-Amino-Substituted N-Fused Imidazoles

Gold-catalyzed formal 1,3-dipolar annulation between readily accessible N-pyridinylsulfilimines and ynamides is reported. A diverse set of imidazole derivatives is prepared from the corresponding sulfilimines and ynamides. These functionalized cyclic products can undergo further transformations to afford diverse imidazole frameworks. Moreover, in situ synthesis is feasible and shows good potential in the synthesis of nucleoside analogues.

Synthesis of bis(halovinyl)benzenes by catalytic olefination

Catalytic olefination of hydrazines of terephthalic and isophthalic aldehydes with polyhaloalkanes afforded the corresponding p- and m-divinylbenzene derivatives bearing halogen atoms and various functional groups at the double bonds. Stereochemical featu

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright

Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles

Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.

Synthesis and photophysical studies of bis-enediynes as tunable fluorophores

We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the π-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.

Reactions with Phosphinealkylenes, XXXIX. - New Methods for the Preparation of 1-Bromoacetylenes and Enynes

1,1-Dibromoolefins 4 are obtained in good yield from the reaction of aldehydes 1 with triphenylphosphane (2) and carbon tetrabromide (3).Reaction of 4 with three moles of methylene(triphenyl)phosphorane (8) leads to the propargylidene(triphenyl)phosphoranes 11 which react with aldehydes to give the enynes 13.The ylides 11 can also prepared via the reaction of bromoacetylenes 7, which can be obtained from 4, with two moles of 8.This reaction sequence allows the synthesis of new retinoids with enyne structures from retinal.