59931-63-4

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 

Downstream Products

• 16616-38-9 1-(3-chlorophenyl)-3-phenyl-2-propyn-1-one 
• 1618678-05-9 ethyl 1-phenyl-2-methyl-4-(3-chlorophenyl)-5-benzyl-1H-pyrrole-3-carboxylate 
• 20426-48-6 (E)-1-(3-chlorophenyl)-3-phenylprop-2-en-1-one 
• 1228040-35-4 3-benzyl-2-(3-chlorophenyl)-1H-imidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

BINOL-Salen-catalyzed highly enantioselective alkyne additions to aromatic aldehydes

(Equation presented) The BINOL-Salen compound (-)-1 can catalyze the addition of both aryl- and alkylalkynes to aromatic aldehydes at room temperature with high enantioselectivity (86-97% ee). The conditions for this catalytic process are both mild and simple. Unlike most other BINOL-based catalysts, using ligand (-)-1 not only avoids heating or cooling but also does not require the addition of Ti(OiPr)4.

Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols

Abstract: A practical synthesis of propargylic alcohols was developed by alkynylation of aldehydes mediated by zinc and allyl bromide. Aromatic, aliphatic and vinyl aldehydes react with phenylacetylene or 1-hexyne to obtain various propargylic alcohols at room temperature in up to 98% yield. This method is characterized with inexpensive materials, wide substrate scope, and mild reaction conditions, and is also easy to scale up. In addition, this protocol is applicable to the alkynylation of α-ketone esters and epoxides to generate α-tertiary-hydroxy esters and α-alkynyl alcohols, respectively. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes

Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the

A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/ cycloisomerization reaction

Development of an efficient synthesis of fully substituted pyrroles via a sequential propargylation/amination/cycloisomerization was accomplished using AgSbF6 as a catalyst. The one-pot three-component reaction of propargylic alcohols, 1,3-dica

A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction

Development of an efficient synthesis of fully substituted pyrroles via a sequential propargylation/amination/cycloisomerization was accomplished using AgSbF6as a catalyst. The one-pot three-component reaction of propargylic alcohols, 1,3-dicar

Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition

The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.

Tandem amination/cycloisomerization of aryl propargylic alcohols with 2-aminopyridines as an expedient route to imidazo[1,2-a]pyridines

A new tandem route leading to imidazo[1,2-a]pyridines has been explored through the direct amination of aryl propargylic alcohols with 2-aminopyridines and their subsequent intramolecular cycloisomerization. A ZnCl2/CuCl system has been develop

A new and general one-pot synthesis of propargyl alcohols from esters

Intermediates easily prepared by partial reduction of various esters with LDBBA as a reducing agent smoothly react with lithium acetylides to give propargyl alcohols, without isolation of partial reduction intermediates, in good yields (73-83%).

Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes

A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl- and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good to high enantioselectivities.

Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex

The readily available and inexpensive new chiral oxazolidine 2a in combination with Ti(OiPr)4 was found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes to generate chiral propargylic alcohols with high enantioselectivities (up to 95%) and excellent yields (up to 98%). The Royal Society of Chemistry.