Direct C–H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis DOI
Lu Wang, Ting Wang, Gui‐Juan Cheng

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(14), P. 7543 - 7551

Published: June 11, 2020

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C–H bonds, facilitating visible light-catalyzed construction a variety ketones. Tetrabutylammonium decatungstate anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested Pd0–PdII–PdIII–PdI–Pd0 pathway revealed regeneration the Pd0 catalyst photocatalyst occurs simultaneously in presence KHCO3. This features low energy barrier, promoting efficient coupling catalytic cycle photocatalytic cycle. The work reported herein suggests great promise for further applications palladium-catalyzed cross-coupling C-H functionalization reactions be successful.

Language: Английский

Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)–H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis DOI Creative Commons
Harunobu Mitsunuma,

Shun Tanabe,

Hiromu Fuse

et al.

Chemical Science, Journal Year: 2019, Volume and Issue: 10(12), P. 3459 - 3465

Published: Jan. 1, 2019

We have developed a catalytic asymmetric nucleophilic allylation of aldehydes using simple alkenes as pronucleophiles without relying on stoichiometric metals.

Language: Английский

Citations

163
Dialkylation of 1,3-Dienes by Dual Photoredox and Chromium Catalysis DOI

J. Luca Schwarz,

Huan‐Ming Huang,

Tiffany O. Paulisch

et al.

ACS Catalysis, Journal Year: 2019, Volume and Issue: 10(2), P. 1621 - 1627

Published: Dec. 18, 2019

The direct conversion of feedstock chemicals into value-added products is broad interest in chemical research. Herein, we present a regioselective and diastereoselective three-component dialkylation 1,3-dienes with Hantzsch esters aldehydes for the synthesis homoallylic alcohols. reaction enabled by dual photoredox chromium catalysis can also be performed enantioselectively employing chromium-bisoxazoline complexes.

Language: Английский

Citations

153
A review of enantioselective dual transition metal/photoredox catalysis DOI
Hong‐Hao Zhang, Hui Chen, Chengjian Zhu

et al.

Science China Chemistry, Journal Year: 2020, Volume and Issue: 63(5), P. 637 - 647

Published: April 1, 2020

Language: Английский

Citations

149
Recent advances in transition-metal-catalysed asymmetric coupling reactions with light intervention DOI

Fu‐Dong Lu,

Jun Chen, Xuan‐Feng Jiang

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(22), P. 12808 - 12827

Published: Jan. 1, 2021

Transition metal-catalysed asymmetric coupling has been established as a robust tool for constructing complex organic molecules. Although this area extensively studied, the development of efficient protocols to construct stereogenic centres with excellent regio- and enantioselectivities is highly desirable remains challenging. Asymmetric transition metal catalysis light intervention provides practical alternative strategy current methods considerably expands synthetic utility result abundant feedstocks mild conditions. This tutorial review comprehensively summarizes recent advances in transition-metal-catalysed reactions intervention; particular, concise analysis substrate scope mechanistic scenarios governing stereocontrol discussed.

Language: Английский

Citations

141
Visible Light Assisted Radical‐Polar/Polar‐Radical Crossover Reactions in Organic Synthesis DOI
Shivani Sharma, Jitender Singh, Anuj Sharma

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(13), P. 3146 - 3169

Published: April 10, 2021

Abstract Chemists are generally familiar with polar reactions and radical reactions, in comparison, underdeveloped. In the last few years, however, novel concept of amalgamation above two form radical‐polar crossover (RPCO) polar‐radical (PRCO) has emerged as a valuable powerful tool. This methodology tends to bridge gap between well overcomes limitations both traditional chemistry. By bringing together unorthodox chemistry radicals orthodox carbocations carbanions, green quotient such is significantly improved. The development shaping up this area years synthetically important transformations summarised review. magnified image

Language: Английский

Citations

124
Metallaphotoredox catalysis for sp3C–H functionalizations through hydrogen atom transfer (HAT) DOI
Jingchang Zhang, Magnus Rueping

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(12), P. 4099 - 4120

Published: Jan. 1, 2023

sp 3 C–H functionalizations under the combination of photocatalytic HAT and transition metal catalysis.

Language: Английский

Citations

89
Efficient and Direct Functionalization of Allylic sp3 C−H Bonds with Concomitant CO2 Reduction DOI
Ming–Yu Qi, Yi‐Jun Xu

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(41)

Published: Aug. 26, 2023

Solar-driven CO2 reduction integrated with C-C/C-X bond-forming organic synthesis represents a substantially untapped opportunity to simultaneously tackle carbon neutrality and create an atom-/redox-economical chemical synthesis. Herein, we demonstrate the first cooperative photoredox catalysis of efficient tunable syngas, paired direct alkylation/arylation unactivated allylic sp3 C-H bonds for accessing C-C products, over SiO2 -supported single Ni atoms-decorated CdS quantum dots (QDs). Our protocol not only bypasses additional oxidant/reductant pre-functionalization substrates, affording broad products moderate excellent yields, but also produces syngas CO/H2 ratios (1 : 2-5 1). Such win-win coupling highlights high atom-, step- redox-economy, good durability, illuminating tantalizing possibility renewable sunlight-driven feedstocks manufacturing industry.

Language: Английский

Citations

82
Light-empowered contra-thermodynamic stereochemical editing DOI

Peng‐Zi Wang,

Wen‐Jing Xiao, Jia‐Rong Chen

et al.

Nature Reviews Chemistry, Journal Year: 2022, Volume and Issue: 7(1), P. 35 - 50

Published: Nov. 16, 2022

Language: Английский

Citations

77
Light-driven C–O coupling of carboxylic acids and alkyl halides over a Ni single-atom catalyst DOI
Mark A. Bajada, Giovanni Di Liberto, Sergio Tosoni

et al.

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(11), P. 1092 - 1103

Published: June 15, 2023

Language: Английский

Citations

43
Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization DOI Creative Commons
Siyuan Tang,

Z. Z. Wang,

Ao Yu

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 4, 2025

Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet be fully explored. Herein, we present successful description photoredox/Cr-catalyzed three-component (hetero)arylalkylation 1,3-dienes functionalization. A diverse array homoallylic alcohols could obtained good excellent yields, accompanied by outstanding enantioselectivity. asymmetric build two simultaneously and demonstrates broad substrate tolerance, accommodating various drug-derived aldehydes, (hetero)aromatics, 1,3-diene derivatives. Preliminary mechanistic studies indicate the involvement radical intermediate, allylic chromium species reacting aliphatic aromatic aldehydes Zimmerman–Traxler transition states enabled dual photoredox catalysis. ongoing Here, authors photoredox- chromium-catalyzed

Language: Английский

Citations

2