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.

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.

Synthesis of Novel Annulated Hymenialdisine Analogues via Palladium-Catalyzed Cross-Coupling Reactions with Aryl Boronic Acids

Synlett ◽  
2009 ◽  
Vol 2010 (02) ◽  
pp. 211-214
Author(s):  
Man-Kin Tse ◽  
Naveenkumar Mangu ◽  
Anke Spannenberg ◽  
Matthias Beller
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Palladium-catalyzed cross-coupling reactions of aryl boronic acids with aryl halides in water

2009 ◽  
Vol 21 ◽  
pp. S124-S126 ◽  
Author(s):  
Shaoyan WANG ◽  
Zhiqiang ZHANG ◽  
Zhizhi HU ◽  
Yue WANG ◽  
Peng LEI ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Synthesis of Ortho-Arylated and Alkenylated Benzamides by Palladium-Catalyzed Denitrogenative Cross-Coupling Reactions of 1,2,3-Benzotriazin-4(3H)‑Ones with Organoboronic Acids

2021 ◽  
Author(s):  
Hari Balakrishnan Madasamy ◽  
Kanagaraj Madasamy ◽  
Velayutham Sankar ◽  
Mahesh kumar Ravva ◽  
Mannathan Subramaniyan
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Organoboronic Acids ◽  
Palladium Catalyzed

An efficient palladium-catalyzed denitrogenative Suzuki-Miyaura type cross-coupling of 1,2,3-benzotriazin-4(3H) ones with organoboronic acid is described. The reaction is compatible with various aryl and alkenyl boronic acids affording ortho-arylated and alkenylated...

scholarly journals Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

2013 ◽  
Vol 9 ◽  
pp. 2470-2475 ◽  
Author(s):  
Ju Hee Kim ◽  
Su Jeong Choi ◽  
In Howa Jeong
Keyword(s):  
Cross Coupling ◽  
Catalytic Amount ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Cross Coupling Reactions ◽  
The Cross ◽  
High Yields

The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh3)2Cl2 and Na2CO3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3.

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