The Synthesis of Novel Oligomer 4,8-Di(4-hexyl-2-thienyl)-2λ4δ2-Benzo[1,2-c;4,5-c’]bis[1,2,5]-Thiadiazole

2012 ◽  
Vol 602-604 ◽  
pp. 696-699
Author(s):  
Xiao Xiao Zhuang ◽  
Xiao Long Lei ◽  
Xiao Xia Sun
Keyword(s):  
Side Chains ◽  
Coupling Reactions ◽  
Low Bandgap ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
High Yields ◽  
Bandgap Materials

Heterocyclic oligomer based on BBT bearing solubilizing side chains have been synthesized in high yields over six steps from readily available starting materials. This approach offers a much milder, shorter, and more efficient route to BBT derivatives than current methods. This unit can then be used in the synthesis of low bandgap materials via palladium-catalyzed coupling reactions.

Synthesis of a Novel Acceptor Unit for D-A Type Polymers: 4,8-Dibromobenzo-[1,2-c;4,5-c′]bis[1,2,5]thiadiazole

2012 ◽  
Vol 482-484 ◽  
pp. 1221-1224 ◽  
Author(s):  
Xiao Xia Sun ◽  
Xiao Xiao Zhuang ◽  
Ya Li Ren
Keyword(s):  
Synthetic Approach ◽  
Coupling Reactions ◽  
Low Bandgap ◽  
Common Precursor ◽  
Palladium Catalyzed ◽  
Bandgap Materials

A synthetic approach to synthesize 4,8-Dibromobenzo-[1,2-c;4,5-c’] bis[1,2,5]thiadiazole from a common precursor 2,1,3-Benzothiadiazole is reported. This unit can then be used in the synthesis of low bandgap materials via palladium-catalyzed coupling reactions.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

scholarly journals Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2740 ◽  
Author(s):  
Abdelaziz Ejjoummany ◽  
Rabia Belaroussi ◽  
Ahmed El Hakmaoui ◽  
Mohamed Akssira ◽  
Gérald Guillaumet ◽  
...  
Keyword(s):  
Process Optimization ◽  
Cross Coupling ◽  
Regioselective Synthesis ◽  
Coupling Reactions ◽  
Pyrimidine Derivatives ◽  
Release Process ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
High Yields

The design of some novel di-(het)arylated-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out in C-4 by in situ C-O activation and next in C-2 by a methylsulfur release. Process optimization furnished conditions leading to products in high yields. The scope and limitations of the methodologies were evaluated and the final compounds characterized.

Palladium-Catalyzed Asymmetric Heck–Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3269-3276
Author(s):  
Ze-Zhen Jiang ◽  
Yang-Jie Jiang ◽  
Juan Du ◽  
Di Chen ◽  
Chang-Hua Ding ◽  
...  
Keyword(s):  
Optically Active ◽  
Diazonium Salts ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
High Yields

A palladium-catalyzed asymmetric Heck–Matsuda reaction of N-Boc-1,4-dihydroquinolines and aryl diazonium tetrafluoroborates is realized in moderate to high yields and with high enantioselectivities. The method provides an efficient route to access optically active 2-arylhydroquinolines.

An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: insights from experiment and computation

2016 ◽  
Vol 14 (3) ◽  
pp. 895-904 ◽  
Author(s):  
Daoshan Yang ◽  
Yuxia Liu ◽  
Pengfei Sun ◽  
Ning Zhang ◽  
Wei Wei ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reactions ◽  
Heck Coupling ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
Type Coupling ◽  
Regioselective Functionalization

This study reports the Pd-catalyzed decarboxylative Heck-type coupling of 3-chlorobenzo[b]thiophene-2-carboxylic acids with styrenes.

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

2016 ◽  
Vol 69 (6) ◽  
pp. 618 ◽  
Author(s):  
Bhaskaran Savitha ◽  
Ayyiliath. M. Sajith ◽  
M. Nibin Joy ◽  
K.K. Abdul Khader ◽  
A. Muralidharan ◽  
...  
Keyword(s):  
Comparative Study ◽  
Cross Coupling ◽  
Reaction Rates ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Coupling Process ◽  
Substantial Role ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
High Yields

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.

A Novel Access to Tertiary and Secondary ortho-Aminophenylphosphines by Protected Group Synthesis and Palladium Catalyzed P-C Coupling Reactions

2001 ◽  
Vol 56 (4-5) ◽  
pp. 347-353 ◽  
Author(s):  
Antonella Heßler ◽  
Konstantin W. Kottsieper ◽  
Stefan Schenk ◽  
Michael Tepper ◽  
Othmar Stelzer
Keyword(s):  
Coupling Reaction ◽  
Secondary Phosphine ◽  
Coupling Reactions ◽  
The Novel ◽  
Protected Group ◽  
Metallic Lithium ◽  
Subsequent Hydrolysis ◽  
Palladium Catalyzed ◽  
High Yields

Abstract The dilithium salt 1a formed by ortho-metallation of N-tert-butoxycarbonylaniline (BOC-aniline) 1 with two equivalents of tert-butyllithium reacts with the chlorophosphines Ph3-nPCln (n = 1 -3) to yield the BOC protected ortho-aminophenylphosphines 2 - 4 in high yields. On deprotection of 2 - 4 with trimethylchlorosilane in the presence of phenol the HCl adducts of the ortho-aminophenylphosphines 5 -7 are formed which may be deprotonated with KOH or NaOH to give the neutral phosphines 5a -7a. The novel secondary phosphine 8 with two ortho-aminophenyl groups is accessible by cleavage of the P-C bond in 7a with metallic lithium and subsequent hydrolysis. The bifunctional P,N ligands 6 or 6a are alternatively accessible by Pd-catalyzed P-C coupling of ortho-iodoaniline with phenylphosphine. If a 1:1 stoichiometry is employed in the coupling reaction of ortho-iodoaniline and phenylphosphine the chiral secondary phosphine 9 is formed.

Palladium-Catalyzed Decarboxylative Csp2–Csp2 Cross-Coupling Reactions: An Efficient Route for Synthesis of Azaisoflavone Derivatives

2015 ◽  
Vol 145 (8) ◽  
pp. 1634-1642 ◽  
Author(s):  
Chengcai Xia ◽  
Yong Yang ◽  
Zhenjiang Wei ◽  
Wenbo Yu ◽  
Hanxiao Liao ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Efficient Route
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