166663-45-2

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 106-48-9 4-chloro-phenol 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 1357115-38-8 4-((trimethylsilyl)ethynyl)phenyl trifluoromethanesulfonate 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 2926-30-9 sodium triflate 
• 536-74-3 phenylacetylene 
• 839686-54-3 4-<<-tert-butyldimethylsiloxy)phenyl>ethynyl>benzene 

Downstream Products

• 1026638-10-7 4-(4-Phenylethynyl-phenylethynyl)-benzoic acid 2,4,5-trichloro-phenyl ester 
• 1027986-99-7 4-(4-Phenylethynyl-phenylethynyl)-benzoic acid 
• 166663-41-8 methyl 4-<<4'-(phenylethynyl)phenyl>ethynyl>benzoate 

Relevant academic research and scientific papers

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Zinc chloride-promoted aryl bromide-alkyne cross-coupling reactions at room temperature

(Chemical Equation Presented) Substoichiometric amounts of ZnCl2 promote the room temperature, Pd/P(t-Bu)3-catalyzed cross-coupling of aryl bromides with alkynes. Pd(I) dimer 1 is demonstrated to be a particularly active precatalyst for this reaction. The reaction is general for a wide variety of aryl bromides.

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both hom

Dichloro[(2-dimethylamino)propyldiphenylphosphine]palladium(II) (PdCl2(alaphos)): An efficient catalyst for cross-coupling of aryl triflates with alkynyl grignard reagents

Dichloro[(2-dimethylamino)propyldiphenylphosphine]palladium (PdCl2(alaphos)) was found to be much more effective as catalyst than other palladium complexes for cross-coupling of aryl triflates with alkynyl Grignard reagents. Reaction of bromoaryl triflates with alkynyl Grignard reagents in the presence of PdCl2(alaphos) catalyst gave high yields of alkynyl arene bromides, which were formed by selective replacement of triflate by alkynyl group.

Semisynthetic Chemical Modification of the Antifungal Lipopeptide Echinocandin B (ECB): Structure-Activity Studies of the Lipophilic and Geometric Parameters of Polyarylated Acyl Analogs of ECB

Echinocandin B (ECB) is a lipopeptide composed of a complex cyclic peptide acylated at the N-terminus by linoleic acid.Enzymatic deacylation of ECB provided the peptide "nucleus" as a biologically inactive substrate from which novel ECB analogs were generated by chemical reacylation at the N-terminus.Varying the acyl group revealed that the structure and physical properties of the side chain, particularly its geometry and lipophlicity, played a pivotal role in determining the antifungal potency properties of the analog.Using CLOGP values to describe and compare the lipophlicities of the side chain fragments, it was shown that values of >3.5 were required for expression of antifungal activity.Sercondly, a linearly rigid geometry of the side chain was the most effective shape in enhancing the antifungal potency.Using these parameters as a guide, a variety of novel ECB analogs were synthesized which included arylacyl groups that incorporated biphenyl, terphenyl, tetraphenyl, and arylethynyl groups.Generally the glucan synthase inhibition by these analogs correlated well with in vitro and in vivo activities and was likewise influenced by the structure of the side chain.These structural variations resulted in enhancement of antifungal activity in both in vitro and in vivo assays.Some of these analogs, including LY303336 (14a), were effective by the oral route of administartion.