A Novel Indium-Catalyzed Three-Component Reaction: General and Efficient One-Pot Synthesis of Substituted Pyrroles

A convenient and general approach towards the synthesis of substituted pyrroles from propargylic acetates, silyl enol ethers, and primary amines was described. This novel transformation was catalyzed by indium trichloride in a one-pot synthesis, and high yields of various pyrrole derivatives were obtained.National Natural Science Foundation of China [20772098

Iron(III) Chloride-catalyzed Nucleophilic Substitution of Propargylic Alcohols: A General and Efficient Approach for the Synthesis of 1,4-Diynes

A wide variety of 1,4-diynes have been constructed via a novel FeCl(3)-catalyzed coupling reaction of propargylic alcohols with alkynylsilanes. This synthetic approach provides a general, efficient, and economical route to 1,4-cliynes.National Natural Science Foundation of China[20772098, 21072159

Cyclization of samarium diiodide-generated vinyl radicals in 6-(π-exo)-exo-dig mode

Radical cyclization of vinyl iodides in 6-(pi-exo)-exo-dig mode were effected by SmI2 to give exo-cyclic dienes fused to six-membered rings

Solvent-free solid acid-catalyzed nucleophilic substitution of propargylic alcohols: a green approach for the synthesis of 1,4-diynes

Acid-treated K10 montmorillonite (H-K10 mont) exhibited an outstanding catalytic activity in the nucleophilic substitution of propargylic alcohols with alkynylsilanes. The reactions were carried out under solvent-free conditions, and the solid catalyst was reusable with retention of its high activity. This method provides a green and rapid route to 1,4-diynes.National Natural Science Foundation of China [20772098

Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols

Three different substituted thiazoles have been successfully synthesized from readily available propargylic alcohols. Various secondary propargylic alcohols or tertiary propargylic alcohols participated well in the reaction, providing the desired products in good yields. This method provides a flexible and rapid route to substituted thiazoles.National Natural Science Foundation of China [20772098]; Program for New Century Excellent Talents in Fujian Province Universit

One-pot highly efficient synthesis of substituted pyrroles and N-bridgehead pyrroles by zinc-catalyzed multicomponent reaction

A convenient zinc(II) chloride-catalyzed regioselective propargylation/amination/cycloisomerization process has been developed for the synthesis of substituted pyrrole derivatives from propargylic acetates, enoxysilanes and primary amines. Various aromatic and aliphatic propargylic acetates participate well in the reaction, providing the propargylation/amination/cycloisomerization products in good yields with complete regioselectivity. The one-pot multicomponent coupling reaction furnishes substituted pyrroles in high yields by circumventing the intermediates' isolation. Zinc( II) chloride acts as a multifunctional catalyst and catalyzes three mechanistically distinct processes in a single-pot. The protocol developed has been extended to the synthesis of N-bridgehead pyrroles containing polycyclic fragments.National Natural Science Foundation of China [20772098]; Fujian Province Universit

FeCl3-Catalyzed Propargylation-Cycloisomerization Tandem Reaction: A Facile One-Pot Synthesis of Substituted Furans

An efficient FeCl3-catalyzed tandem propargylation-cycloisomerization reaction of propargylic alcohols or acetates with 1,3-dicarbonyl compounds, leading to the synthesis of substituted furans, has been developed.National Natural Science Foundation of China [20772098, 30572250]; Fujian Province Universit

BiCl3-catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles

A general and efficient BiCl3-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction of C - C, C - O, C - S and C - N bonds, has been developed

Selective synthesis of 4-(sulfonyl)-methyl-1H-pyrazoles and (E)-4,5-dihydro-1H-pyrazoles from N-allenic sulfonylhydrazones

National Natural Science Foundation of China [21272190]; PCSIRT in University; NFFTBS [J1210014]Selective synthesis of 4-(sulfonyl)-methyl-1H-pyrazoles and (E)-4,5-dihydro-1H-pyrazoles from N-allenic sulfonylhydrazones with sulfonyl group migrations has been developed. A key feature of these reactions is that the migrations of the sulfonyl groups to different positions can be controlled by changing the Lewis acids

Copper(II)-Catalyzed Synthesis of Pyrimidines from Propargylic Alcohols and Amidine: A Propargylation-Cyclization-Oxidation Tandem Reaction

A new approach to the tandem synthesis of 2,4-disubstituted or 2,4,6-trisubstituted pyrimidines from propargylic alcohols with amidine is described. This reaction is catalyzed by 20 mol% Cu(OTf)(2) to give pyrimidines in moderate to good yields via a propargylation-cyclization-oxidation tandem sequence.National Natural Science Foundation of China[21072159]; Science & Technology Bureau of Xiamen[3502Z20093007]; NFFTBS[J1030415