Computational Clarification of Synergetic RuII/CuI-Metallaphotoredox Catalysis in C(sp3)–N Cross-Coupling Reactions of Alkyl Redox-Active Esters with Anilines

ACS Catalysis ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 5030-5041 ◽  
Author(s):  
Yanhong Liu ◽  
Yiying Yang ◽  
Rongxiu Zhu ◽  
Dongju Zhang
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Active Esters ◽  
Cross Coupling Reactions ◽  
Redox Active

Visible-light-induced iodine anion catalyzed decarboxylative/ deaminative C-H alkylation of enamides

2021 ◽  
Author(s):  
Jia-Xin Wang ◽  
Ya-Ting Wang ◽  
Hao Zhang ◽  
Ming-Chen Fu
Keyword(s):  
Amino Acid ◽  
Visible Light ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Active Esters ◽  
Cross Coupling Reactions ◽  
Redox Active ◽  
Iodine Anion

A visible-light-induced iodine anion catalyzed C-H stereoselective alkylation of enamides has been developed. Redox-active esters and Katritzky salts of the amino acid are amenable for decarboxylative/deaminative cross-coupling reactions, delivering various...

scholarly journals N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts

2020 ◽  
Vol 11 (12) ◽  
pp. 3192-3197 ◽  
Author(s):  
Inwon Kim ◽  
Honggu Im ◽  
Hyeonyeong Lee ◽  
Sungwoo Hong
Keyword(s):  
Catalytic System ◽  
Cross Coupling ◽  
Pyridinium Salts ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Redox Active

By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

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.

Phosphino-Triazole Ligands for Palladium-Catalysed Cross-Coupling

2018 ◽  
Author(s):  
Yiming Zhao ◽  
Huy van Nguyen ◽  
Louise Male ◽  
Philip Craven ◽  
Benjamin R. Buckley ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Cross Coupling ◽  
Product Formation ◽  
Coupling Reactions ◽  
Volume Determination ◽  
Online Tool ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Modelling Approaches

<div>Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesised and used as ligands for palladium-catalysed Suzuki-Miyaura cross-coupling reactions. Bulky substrates were tested, and lead-like product formation was demonstrated. The online tool SambVca 2.0 was used to assess steric parameters of ligands and preliminary buried volume determination using XRD obtained data in a small number of cases proved to be informative. Two modelling approaches were compared for the determination of</div><div>the buried volume of ligands where XRD data was not available. An approach with imposed steric restrictions was found to be superior in leading to buried volume determinations that closely correlate with observed reaction conversions. The online tool LLAMA was used to determine lead-likeness of potential Suzuki-Miyaura cross-coupling products, from which ten of the most lead-like were successfully synthesised. Thus, confirming these readily accessible triazole-containing phosphines as highly suitable ligands for reaction screening and optimisation in drug discovery campaigns.</div>

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