89458-21-9

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 6738-06-3 phenylethynylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 925-90-6 ethylmagnesium bromide 
• 591-50-4 iodobenzene 
• 1482-15-1 3,4-dimethylpent-1-yn-3-ol 

Downstream Products

• 1180663-18-6 [3,4-dimethyl-3-(2-methylallyloxy)pent-1-ynyl]benzene 
• 1360703-75-8 (Z)-3-benzoyl-4-benzylidene-5-isopropyl-5-methyloxazolidin-2-one 
• 1564275-29-1 (Z)-3,4-dimethyl-1-phenylpent-1-en-3-ol 
• 1220698-70-3 3,4-dimethyl-1-phenyl-1-pentyn-3-yl formate 
• 124475-77-0 2-(2,2,3-Trimethyl-3-phenylethynyl-aziridin-1-yl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

Metal-Free Regioselective Chloroazidation of Internal Alkynes

A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.

Palladium(II) complex for catalyzing sonogashira coupling reactions and a method thereof

A palladium(II) complex which catalyzes the Sonogashira coupling reaction efficiently under aerobic condition and a method of employing the palladium(II) complex to synthesize internal alkynes. The palladium(II) complex is an effective catalyst for the co

Tert-butoxy rare earth/sodium impurity bimetallic complex, as well as preparation method and use thereof

The invention discloses a tert-butoxy rare earth/sodium hetero-bimetallic complex as well as a preparation method and use thereof. The molecular formula of the tert-butoxy rare earth/sodium hetero-bimetallic complex is LnNa8[OC(CH3)3]10(OH), and Ln repres

Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the p

Scope and mechanistic analysis of the enantioselective synthesis of allenes by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and propargylic alcohols

Rhodium-catalyzed reactions of tertiary propargylic alcohols with methyl aryl- and styryldiazoacetates result in tandem reactions, consisting of oxonium ylide formation followed by [2,3]-sigmatropic rearrangement. This process competes favorably with the standard O-H insertion reaction of carbenoids. The resulting allenes are produced with high enantioselectivity (88-98% ee) when the reaction is catalyzed by the dirhodium tetraprolinate complex, Rh 2(S-DOSP)4. Kinetic resolution is possible when racemic tertiary propargylic alcohols are used as substrates. Under the kinetic resolution conditions, the allenes are formed with good diastereoselectivity and enantioselectivity (up to 6.1:1 dr, 88-93% ee), and the unreacted alcohols are enantioenriched to 65-95% ee. Computational studies reveal that the high asymmetric induction is obtained via an organized transition state involving a two-point attachment: ylide formation between the alcohol oxygen and the carbenoid and hydrogen bonding of the alcohol to a carboxylate ligand. The 2,3-sigmatropic rearrangement proceeds through initial cleavage of the O-H bond to generate an intermediate with close-lying open-shell singlet, triplet, and closed-shell singlet electronic states. This intermediate would have significant diradical character, which is consistent with the observation that the 2,3-sigmatropic rearrangement is favored with donor/acceptor carbenoids and more highly functionalized propargylic alcohols.

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.

Synthesis of propargylic alcohols by base promoted alkynylation of ketones with ethynylbenzene using ionic liquid [(bmim) PF6]

A mild and efficient addition of ethynylbenzene with ketones using KOH in ionic liquid 1-butyl-3-methylimidazolium hexaflurophosphate [(bmim) PF 6] gives propargylic alcohols in high yields.

Mild and solvent-free alkynylation of ketones on the KF/alumina

The solvent-free alkynylation of various ketones on the surface of KF/alumina under mild conditions is described. Copyright Taylor & Francis, Inc.

Me2Zn-mediated addition of acetylenes to aldehydes and ketones

Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave "ligand like". Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.