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.

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.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines

Synlett ◽  
1999 ◽  
Vol 1999 (7) ◽  
pp. 1145-1147 ◽  
Author(s):  
Martina Havelková ◽  
Michal Hocek ◽  
Michal Česnek ◽  
Dalimil Dvořák
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

A simple and efficient synthesis of 5′-(2H3)olivetol

1987 ◽  
Vol 65 (1) ◽  
pp. 189-190 ◽  
Author(s):  
Michel Girard ◽  
David B. Moir ◽  
John W. ApSimon
Keyword(s):  
Title Compound ◽  
Cross Coupling ◽  
Side Chain ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Cross Coupling Reactions

The title compound 1 was prepared in 13% overall yield starting from the commercially available and inexpensive 3,5-dimethoxybenzoic acid (4). The n-pentyl side chain was elaborated from cross-coupling reactions between halides.

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