Cobalta‐Electrocatalyzed C−H Activation in Biomass‐Derived Glycerol: Powered by Renewable Wind and Solar Energy DOI Creative Commons
Tjark H. Meyer, Gleb A. Chesnokov, Lutz Ackermann

et al.

ChemSusChem, Journal Year: 2020, Volume and Issue: 13(4), P. 668 - 671

Published: Jan. 9, 2020

Abstract Aqueous glycerol was identified as a renewable reaction medium for metalla‐electrocatalyzed C−H activation powered by sustainable energy sources. The solvent employed cobalt‐catalyzed C−H/N−H functionalizations under mild conditions. cobalta‐electrocatalysis manifold occurred with high levels of chemo‐ and positional selectivity allowed electrochemical activations broad substrate scope. resource economy this strategy considerably substantiated the direct use solar wind energy.

Language: Английский

Renewable resources for sustainable metallaelectro-catalysed C–H activation DOI Creative Commons
Ramesh C. Samanta, Tjark H. Meyer, Inke Siewert

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(33), P. 8657 - 8670

Published: Jan. 1, 2020

The merger of C–H activation with electrosynthesis, powered by renewable energies and resources, will guide towards a sustainable future.

Language: Английский

Citations

84

Green strategies for transition metal-catalyzed C–H activation in molecular syntheses DOI Creative Commons
Uttam Dhawa, Nikolaos Kaplaneris, Lutz Ackermann

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(17), P. 4886 - 4913

Published: Jan. 1, 2021

Sustainable strategies for the activation of inert C–H bonds towards improved resource-economy.

Language: Английский

Citations

81

Electro‐Synthesis of Organic Compounds with Heterogeneous Catalysis DOI Creative Commons
Tariq Ali, Haiyan Wang, Waseem Iqbal

et al.

Advanced Science, Journal Year: 2022, Volume and Issue: 10(1)

Published: Nov. 18, 2022

Electro-organic synthesis has attracted a lot of attention in pharmaceutical science, medicinal chemistry, and future industrial applications energy storage conversion. To date, there not been detailed review on electro-organic with the strategy heterogeneous catalysis. In this review, most recent advances synthesizing value-added chemicals by catalysis are summarized. An overview electrocatalytic oxidation reduction processes as well paired electrocatalysis is provided, anodic alcohols (monohydric polyhydric), aldehydes, amines discussed. This also provides in-depth insight into cathodic carboxylates, carbon dioxide, CC, C≡C, reductive coupling reactions. Moreover, electro-synthesis methods, including parallel paired, sequential divergent convergent electrolysis, Additionally, strategies developed to achieve high electrosynthesis efficiency associated challenges addressed. It believed that promising direction organic electrochemistry, offering numerous opportunities develop new reaction methods.

Language: Английский

Citations

61

Divergent rhodium-catalyzed electrochemical vinylic C–H annulation of acrylamides with alkynes DOI Creative Commons

Yi‐Kang Xing,

Xinran Chen, Qi‐Liang Yang

et al.

Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)

Published: Feb. 10, 2021

α-Pyridones and α-pyrones are ubiquitous structural motifs found in natural products biologically active small molecules. Here, we report an Rh-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes, affording cyclic good to excellent yield. Divergent syntheses α-pyridones imidates accomplished by employing N-phenyl N-tosyl as substrates, respectively. Additionally, regioselectivities achieved when using unsymmetrical alkynes. This process is environmentally benign compared traditional transition metal-catalyzed annulations because it avoids the use stoichiometric metal oxidants. DFT calculations elucidated reaction mechanism origins substituent-controlled chemoselectivity. The sequential activation alkyne insertion under rhodium catalysis leads seven-membered ring vinyl-rhodium intermediate. intermediate undergoes either classic neutral concerted reductive elimination produce α-pyridones, or ionic stepwise pathway imidates.

Language: Английский

Citations

59

Synthesis of P-stereogenic cyclicphosphinic amidesviaelectrochemically enabled cobalt-catalyzed enantioselective C–H annulation DOI
Tao Liu,

Wangqin Zhang,

Chao Xu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3606 - 3614

Published: Jan. 1, 2023

We describe a cobalta-electro-catalyzed enantioselective C–H annulation of arylphosphinamides with alkynes for P-stereogenic compounds via desymmetrization and kinetic resolution processes.

Language: Английский

Citations

40

N,O-Auxiliary Enabled Cobaltaelectro-Catalyzed Atroposelective C–H Annulation DOI

Yuanshuo Zhang,

Shuang‐Liang Liu, Tong Li

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 1 - 9

Published: Dec. 7, 2023

Herein, we disclosed an efficient synthesis of C–N axially chiral pyridine-N-oxides through cobalt-catalyzed enantioselective C–H activation and annulation under electro-oxidative conditions. This protocol is accomplished by using a readily available cobalt(II) catalyst salicyloxazoline (Salox) ligand in undivided cell. The combination electrochemical simple Co/Salox system enabled effective control over the chemo- enantioselectivity process. A broad range benzamides alkynes bearing diverse functional groups are well compatible to deliver products with high yields enantioselectivities (up 97% yield 99% ee). scalability, asymmetric application, transformations demonstrated synthetic practicality. Moreover, photoluminescence properties further highlight potential applications this strategy material development performance enhancement.

Language: Английский

Citations

26

Cobalta-Electrocatalyzed C–H Allylation with Unactivated Alkenes DOI
Uttam Dhawa, Cong Tian, Weizhao Li

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(11), P. 6457 - 6462

Published: May 12, 2020

Versatile and robust cobalt catalysis enabled the electrochemical C–H allylation with nonactivated alkenes. In contrast to precious palladium, rhodium, iridium, ruthenium catalysts that are limited electronically activated styrenes acrylates, we herein disclose cobalt-catalyzed electro-oxidative allylations Thus, allylated benzamides were obtained high levels of chemoselectivity, positional selectivity, regioselectivity in biomass-derived solvent γ-valerolactone. Detailed mechanistic studies provided strong support for a base-assisted internal electrophilic-type substitution mechanism key activation step. The cobaltaelectro-catalysis overall achieved resource-economy by avoiding use stoichiometric chemical oxidants, H2 as only byproduct.

Language: Английский

Citations

60

Cobaltaelectro-catalyzed oxidative allene annulation by electro-removable hydrazides DOI
Ruhuai Mei,

Xinyue Fang,

Liang He

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(9), P. 1393 - 1396

Published: Dec. 23, 2019

An efficient C-H/N-H functionalization with allenes was enabled via versatile electro-oxidative cobalt catalysis. Thus, electrochemical C-H activations were accomplished high levels of chemoselectivity and regioselectivity in an operationally simple undivided cell setup. The user-friendly nature this protocol highlighted by excellent functional group tolerance, electro-reductive removable hydrazide directing easy scalability. Experimental mechanistic studies indicative a facile BIES cobaltation event.

Language: Английский

Citations

55

Ru(II)-Catalyzed C–H Functionalization of N-Hydroxyoximes with 1,3-Diynes Unveils a Regioselective Disparity DOI
Shreemoyee Kumar, Akshay M. Nair, Chandra M. R. Volla

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(6), P. 2141 - 2146

Published: March 6, 2020

A highly selective and convenient Ru(II)-catalyzed C–H bond activation protocol has been demonstrated to access 4-alkynylated isoquinolines, which was so far elusive from 1,3-diynes. Subsequently, the same extended furnish various 4-4′-biisoquinoline motifs. The key feature of this work is regioselective disparity observed during migratory insertion an organoruthenium metallacycle with C3–C4 triple 1,3-diynes resulting in divergent products as compared existing literature.

Language: Английский

Citations

52

Electrochemically Enabled Intramolecular and Intermolecular Annulations of Alkynes DOI
Kai Sun,

Lei Jia,

Yingjie Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(18), P. 3709 - 3726

Published: Aug. 13, 2020

Abstract Electrosynthesis is recognized as one of the most powerful and sustainable methods in organic chemistry. Recently, electrochemically enabled annulations carbon‐carbon triple bonds have been successfully achieved, broadened prospects for application emerging method with cyclization alkynes. Thus, herein we outline recent progress made on In addition, an emphasis scope, limitations mechanisms these reactions this review. magnified image

Language: Английский

Citations

52