67647-96-5

Upstream product

• 109-72-8 n-butyllithium 
• 152710-05-9 5-phenyl-1-pentyn-3-yl methanesulfonate 
• 693-02-7 hex-1-yne 
• 1082069-11-1 methyl 1-phenyl-4-nonyn-3-yl carbonate 
• 144443-10-7 (E)-1-phenyl-4(S_S)-(p-tolylsulfinyl)non-4-en-3(S)-ol mesylate 
• 110-62-3 pentanal 
• 16520-62-0 4-Phenyl-1-butyne 
• 134260-71-2 1-phenylnon-3-yn-5-ol 
• 159087-40-8 2-hex-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 61124-61-6 3-phenylpropanal p-tosylhydrazone 
• 67648-05-9 1-phenylnon-4-yn-3-ol 
• 1265903-92-1 2-[(1-phenylnon-4-yn-3-yl)thio]benzo[d]thiazole 
• 104-53-0 3-phenyl-propionaldehyde 
• 1265904-00-4 2-[(1-phenylnon-4-yn-3-yl)sulfonyl]benzo[d]thiazole 

Relevant academic research and scientific papers

Copper-Catalyzed Propargylic Reduction with Diisobutylaluminum Hydride

A mild and efficient method for the synthesis of allenes through selective copper-catalyzed hydride addition to propargylic chlorides using commercially available diisobutylaluminum hydride has been developed. This transformation, which is promoted by a readily accessible N-heterocyclic carbene-copper complex, provides a wide range of new and versatile functionalized allenes in good to excellent yields with high regio- A nd stereoselectivities.

SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction

Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.

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.

Mild-condition synthesis of allenes from alkynes and aldehydes mediated by tetrahydroisoquinoline (THIQ)

A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthes

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

2-benzothiazolyl propargyl sulfides: Versatile precursors for enantiopure allenes, E-α,β-unsaturated ketones and Z-sulfonylalkenes

A novel, stereospecific route to allenes is described. The approach proceeds via a retro-ene reaction, initiated by lithium aluminium hydride mediated cleavage of benzothiazole from the respective (chiral) 2-benzothiazolyl propargyl sulfone precursors. As

Selective synthesis of allenes and alkynes through ligand-controlled, palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates

Ligand-controlled regioselective palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates is described. A wide range of allenes and alkynes were obtained by using either 1,2-diphenylphosphinoethane (DPPE) or 1,6-bisdiphenylphosphinohexane (DPPH) as a catalyst ligand.

The synthesis of allenes by Cu(i)-catalyzed regio- and stereoselective reduction of propargylic carbonates with hydrosilanes

Cu(i)-catalyzed anti-SN2′-type reduction of internal propargylic carbonates with hydrosilanes affords various di- and trisubstituted allenes with high regioselectivities; the reactions are compatible with functional groups and work efficiently

A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant

The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.

A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides with carbon-carbon bond- formation

Ligand exchange reaction of β-mesyloxy sulfoxides or β-acetoxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with n-BuLi or EtMgBr at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-phenylethenyl p-tolyl sulfoxides.