13633-28-8

Upstream product

• 122-56-5 tributyl borane 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 13633-26-6 4-phenylbut-1-en-3-yne 
• 106-94-5 propyl bromide 
• 693-03-8 n-butyl magnesium bromide 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 591-50-4 iodobenzene 
• 2384-90-9 1,2-Heptadiene 
• 91787-30-3 2-phenylsulphonyl-1-phenylhept-1-ene 
• 74835-43-1 (+/-)-1-phenylhept-1-yn-3-ol acetate 
• 110-62-3 pentanal 
• 536-74-3 phenylacetylene 
• 557-20-0 diethylzinc 
• 1119-90-0 di-n-butylzinc 

Downstream Products

• 1094509-47-3 (+)-(S)-(E)-1-(2-(methylthio)phenyl)-2-styrylhexan-1-one 

Relevant academic research and scientific papers

Negishi Coupling for Highly Selective Syntheses of Allenes via Ligand Effect and Mechanistic Study via SAESI-MS/MS

β-H elimination is an intrinsic problem in transition metal-catalyzed reactions. We describe herein an interesting ligand effect for Et2Zn acting as either ethyl provider or H provider, respectively: by applying SPhos or Gorlos-Phos as the liga

Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followe

Propargyl Hydrazides as Useful Intermediates Leading to Pyrazoles via Reaction with Certain Electrophiles

The reactions of propargyl hydrazides with certain electrophiles successfully led to the regioselective formation of various alkylated hydrazides. Reactions with electrophiles directly afforded the alkylated, chlorinated, brominated, and iodinated pyrazol

Palladium-catalyzed chemoselective allylic substitution, suzuki-miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives

A formidable challenge at the forefront of organic synthesis is the control of chemoselectivity to enable the selective formation of diverse structural motifs from a readily available substrate class. Presented herein is a detailed study of chemoselectivity with palladium-based phosphane catalysts and readily available 2-B(pin)-substituted allylic acetates, benzoates, and carbonates. Depending on the choice of reagents, catalysts, and reaction conditions, 2-B(pin)-substituted allylic acetates and derivatives can be steered into one of three reaction manifolds: allylic substitution, Suzuki-Miyaura cross-coupling, or elimination to form allenes, all with excellent chemoselectivity. Studies on the chemoselectivity of Pd catalysts in their reactivity with boron-bearing allylic acetate derivatives led to the development of diverse and practical reactions with potential utility in synthetic organic chemistry.

CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes

A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted all

Silver(i)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Silver(i) salts mediated stereospecific transformation of optically active propargylamines to axially chiral allenes with excellent enantioselectivities (17 examples with 96-99% ee; one substrate with 91% ee) without subsequent racemization.

Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes

A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.

Integrated chemical process. One-pot preparation of acetylenes by Peterson-sulfone elimination

Integration of silylation of α-sulfonyl carbanion, addition of the anion of the resulting α-silyl sulfone to aldehyde, Peterson elimination, and sulfone elimination leads to one-pot synthesis of acetylenes.

INTRAMOLECULAR ADDITION OF ALKYLLITHIUMS TO ACETYLENES: REGIOSPECIFIC 4-, 5-, and 6-EXO-DIG CYCLIZATIONS

Primary acetylenic alkyllithiums bearing a phenyl substituent on the triple bond, which may be prepared in virtually quantitative yield by low-temperature lithium-iodine interchange, undergo regiospecific exo-dig cyclization via stereoselective syn-additi

Highly Stereoselective Synthesis of Chiral Alkylallenes by Organocopper(I)-Induced Anti 1,3-Substitution of Chiral Propynyl Esters

The synthesis of chiral 1,3-dialkylallenes R1CH=C=CHR2 of high enantiomeric purity, by applying homogeneous reaction between organocopper(I) reagents of type 2CuX>MgX-LiX> and chiral propynyl methanesulfonates or sulfinates at low temperatures in THF, is reported.The reactions are generally fast; typically complete conversion is obtained within a few minutes at -60 deg C.Overall, high anti stereoselectivity is observed.A plausible mechanism is put forward, and comparison is made with the stereochemistry of reactions of comparable substrates with d10 complexes, e.g. of Pd(0).