90733-18-9

Upstream product

• 591-50-4 iodobenzene 
• 6323-87-1 N,N-diisopropylprop-2-yn-1-amine 
• 50-00-0 formaldehyd 
• 108-18-9 diisopropylamine 
• 536-74-3 phenylacetylene 
• 13120-02-0 N,N-diisopropyl selenoformamide 
• 10342-97-9 N,N-diisopropylmethylamine 
• 932-88-7 1-iodo-2-phenylethyne 
• 298-12-4 Glyoxilic acid 
• 3332-08-9 2-isopropyliminopropane 
• 75-09-2 dichloromethane 

Downstream Products

• 2327-99-3 1-phenylpropadiene 
• 1147845-89-3 (E)-[5-(tert-butyldimethylsilyl)-3-phenyl-2-penten-4-ynyl]diisopropylamine 
• 1147846-08-9 (E)-[2-benzylidene-4-(tert-butyldimethylsilyl)-3-butynyl]diisopropylamine 

Relevant academic research and scientific papers

Glyoxylic Acid: A Carboxyl Group-Assisted Metal-Free Decarboxylative Reaction Toward Propargylamines

Readily available propargylamines are not only fundamental building blocks in organic synthesis, but also possess many prominent biological activities. A highly efficient, concise and environmentally benign decarboxylative reaction of glyoxylic acid monohydrate with secondary amines and alkynes has been elaborated, and a variety of propargylamines are delivered in moderate to good yields under metal-free conditions. A mechanism involving a carboxyl group that assists the reactivity of alkynes, which makes the procedure of Michael addition proceeded smoothly, has been proposed.

Gram-Scale Synthesis of Cu(II)@COF via Solid-State Coordination Approach for Catalysis of Alkyne-Dihalomethane-Amine Coupling

A novel covalent organic framework material COF-DM, which contains chelating coordination environments, was synthesized at the gram level under mild conditions. In addition, its Cu(II)-loaded complex of Cu(II)@COF-DM was prepared by impregnating COF-DM in

Synthesis and Application of Silylene-Stabilized Low-Coordinate Ag(I)-Arene Cationic Complexes

We report the first examples of N-heterocyclic silylene-stabilized monocoordinate Ag(I) cationic complexes weakly bound to the free arene rings (C6H6, C6Me6, and C7H8). Further, the application of these electrophilic Ag(I) complexes as catalysts has been investigated toward A3-coupling reactions, which afforded a series of propargylamines in good to excellent yields with low catalyst loading under a solvent-free condition (19 examples).

Zirconocene-Initiated Intramolecular Hydride Transfer in N -Isoalkyl-Substituted Propargylamines

The unusual transformation of N -isoalkyl-substituted propargylamines into alkenylamines under the action of Cp 2 ZrCl 2 and organoaluminum compounds (Me 3 Al, EtAlCl 2) has been observed. The proposed mechanism, involving the N -isoalkyl-substituted propargylamine undergoing zirconocene-initiated intramolecular hydride transfer was supported by B3LYP/6-31G(d)/LanL2DZ calculations.

Recyclable Cu/C3N4 composite catalyzed AHA/A3 coupling reactions for the synthesis of propargylamines

The heterogeneous Cu/C3N4 catalyst was found to be efficient for the synthesis of propargylamines using a three-component coupling reaction of alkynes, CH2Cl2 and amines (AHA) without additional base. Moreover,

Microwave-assisted copper(I) catalyzed A3-coupling reaction: Reactivity, substrate scope and the structural characterization of two coupling products

The application of highly efficient catalyst [{Cu(μ ? I)2Cu}(PPh3)4] for the synthesis of biologically and pharmaceutically important propargylamine derivatives through microwave assisted A3-coupling reaction is

Post-synthetically modified MOF for the A3-coupling reaction of aldehyde, amine, and alkyne

A new heterogeneous NHC catalyst (Ag-NHC-MOF) was synthesized by the post-synthetic modification of an azolium-containing metal-organic framework. The structure of the catalyst was well defined and fully characterized using various techniques such as PXRD, FE-SEM, HR-TEM, XPS, FT-IR, TGA, BET, 1H-NMR, 13C-NMR, EDS, and ICP. The catalyst showed an excellent activity towards the A3-coupling reaction with a broad substrate scope. The A3-coupling reaction was performed under ambient conditions and full conversion was reached within just 1 hour for the model reaction. The heterogeneous silver NHC MOF (Ag-NHC-MOF) catalyst can be recycled and reused at least four times without a significant loss of activity. In comparison with previously reported heterogeneous catalysts applied for the A3-coupling reaction, the Ag-NHC-MOF demonstrates a superior performance for the A3-coupling reaction.

Construction of polymeric Cu(I) N-heterocyclic carbene complex utilizing terpyridine-Fe(II) as linkers: formation of an efficient and recyclable catalyst

A metal-coordination-driven self-assembly using the predesigned building block has been developed. Herein, the catalytic active NHC–Cu(I) units were introduced into the terpyridine metal coordination polymers. The self-assembled architecture, as a heterog

Single and double A3-coupling (aldehyde-amine-alkyne) reaction catalyzed by an air stable copper(I)-phosphole complex

An air stable copper(I)-phosphole complex, [CuCl{2,5-bis(2-thienyl)-1-phenylphosphole}2] (1), was utilized as a catalyst in single and double A3-coupling reactions for preparing mono- and bi-propargylamines. A variety of aldehydes, a

A highly efficient gold-catalyzed photoredox α-C(sp3)-H alkynylation of tertiary aliphatic amines with sunlight

A new α-C(sp3)-H alkynylation of unactivated tertiary aliphatic amines with 1-iodoalkynes as radical alkynylating reagents in the presence of [Au2(μ-dppm)2]2+ in sunlight provides propargylic amines. Based on mechanistic studies, a C-C coupling of an α-aminoalkyl radical and an alkynyl radical is proposed for the C(sp3)-C(sp) bond formation. The mild, convenient, efficient, and highly selective C(sp3)-H alkynylation reaction shows excellent regioselectivity and good functional-group compatibility. A scale-up to gram quantities is possible with sunlight used as a clean and sustainable energy source.