scholarly journals Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

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.

Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon–­Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as ­Electrophiles

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 330-335 ◽  
Author(s):  
Zheng-Jun Quan ◽  
Xi-Cun Wang ◽  
Ming-Xia Liu ◽  
Hai-Peng Gong
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Reactivity ◽  
Attractive Alternative ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon–carbon cross-coupling reaction with arylsilanes to ­realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon−carbon bond construction.

scholarly journals Highly efficient synthesis of 2-substituted benzo[b]furan derivatives from the cross-coupling reactions of 2-halobenzo[b]furans with organoalane reagents

Synthesis ◽  
2021 ◽  
Author(s):  
chang wen ◽  
Qing Han Li ◽  
Chuan Wu ◽  
ruiqiang Luo ◽  
Feng Chen
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Practical Method ◽  
Bioactive Molecules ◽  
Coupling Reactions ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
The Cross

A highly efficient and simple route for the synthesis of 2-substituted benzo[b]furans has been developed by Palladium catalyzed the cross-coupling reaction of 2-halobenzo[b]furans with aryl, alkynyl and alkylaluminum reagents. Various 2-aryl, 2-alkynyl and 2-alkyl substituted benzo[b]furans derivatives can be obtained with 23-97% isolated yields using 2-3 mol% PdCl2/ 4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[b]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl trimethylsilanyl and benzyl groups worked efficiently with 2-halobenzo[b]furans as well, and three bioactive molecules with 2-substituted benzo[b]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[b]furans derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex

2018 ◽  
Vol 2 (3) ◽  
pp. 591-596 ◽  
Author(s):  
Shuichi Suzuki ◽  
Fumiya Nakamura ◽  
Takeshi Naota
Keyword(s):  
Zinc Complex ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Nitroxide Radical ◽  
Synthetic Method ◽  
Coupling Reactions ◽  
Nitronyl Nitroxide ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

We have developed an efficient synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via palladium-catalyzed cross-coupling reactions with a zinc complex of the parent nitronyl nitroxide radical anion.

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.

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