Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes DOI

Caizhe Shi,

Fusheng Li, Yuqing Chen

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(5), P. 2992 - 2998

Published: Feb. 22, 2021

The concept of "umpolung" reactivity π-allylmetal complexes has been developed as a powerful method for the allylation aldehydes. This paper describes photocatalytic umpolung strategy synthesis nucleophilic allylcobalt through single-electron-transfer (SET) process. enables metallaphotoredox carbonyls with allyl acetate using organic N,N-diisopropylethylamine terminal reductant bypassing use stoichiometric amount metals. Ultraviolet–visible spectroscopy was used to monitor redox changes cobalt in reaction.

Language: Английский

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis DOI
Amy Chan, Ian B. Perry, Noah B. Bissonnette

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1485 - 1542

Published: Nov. 18, 2021

The merger of photoredox catalysis with transition metal catalysis, termed metallaphotoredox has become a mainstay in synthetic methodology over the past decade. Metallaphotoredox combined unparalleled capacity for bond formation broad utility photoinduced electron- and energy-transfer processes. Photocatalytic substrate activation allowed engagement simple starting materials metal-mediated bond-forming Moreover, electron or energy transfer directly key organometallic intermediates provided novel modes entirely complementary to traditional catalytic platforms. This Review details contextualizes advancements molecule construction brought forth by metallaphotocatalysis.

Language: Английский

Citations

1158

Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis DOI Creative Commons

Megan Amy Bryden,

Eli Zysman‐Colman

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(13), P. 7587 - 7680

Published: Jan. 1, 2021

Organic compounds that show Thermally Activated Delayed Fluorescence (TADF) have become wildly popular as next generation emitters in organic light-emitting diodes (OLEDs), but since 2016, received significant and increasing attention photocatalysts.

Language: Английский

Citations

340

Recent advances in photoredox and nickel dual-catalyzed cascade reactions: pushing the boundaries of complexity DOI Creative Commons
Chen Zhu, Huifeng Yue, Lingling Chu

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(16), P. 4051 - 4064

Published: Jan. 1, 2020

Cascade reactions that produce multiple chemical bonds in one synthetic operation are important the efficient construction of complex molecules.

Language: Английский

Citations

305

Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts DOI
Lars Süße, Brian M. Stoltz

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(7), P. 4084 - 4099

Published: Feb. 11, 2021

Asymmetric allylic alkylation mediated by transition metals provides an efficient strategy to form quaternary stereogenic centers. While this transformation is dominated the use of second- and third-row (e.g., Pd, Rh, Ir), recent developments have revealed potential first-row metals, which provide not only a less expensive potentially equally alternative but also new mechanistic possibilities. This review summarizes examples for assembly stereocenters using prochiral substrates hard, achiral nucleophiles in presence copper complexes highlights complementary approaches with soft, catalyzed chiral cobalt nickel complexes.

Language: Английский

Citations

271

Transition metal-catalysed allylic functionalization reactions involving radicals DOI
Huan‐Ming Huang, Peter Bellotti, Frank Glorius

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(17), P. 6186 - 6197

Published: Jan. 1, 2020

In this tutorial review, different types of transition metal-catalysed allylic functionalization reactions involving radicals are highlighted.

Language: Английский

Citations

190

The Merger of Photoredox and Cobalt Catalysis DOI Open Access
M. Kojima, Shigeki Matsunaga

Trends in Chemistry, Journal Year: 2020, Volume and Issue: 2(5), P. 410 - 426

Published: Feb. 13, 2020

Language: Английский

Citations

152

Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis DOI
Yan-Lin Li, Shiqi Zhang, Jie Chen

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(19), P. 7306 - 7313

Published: May 5, 2021

A Co-catalyzed highly regio- and enantioselective reductive coupling of alkynes aldehydes has been developed under visible light photoredox dual catalysis. variety enantioenriched allylic alcohols have obtained by using unsymmetrical internal commercially available catalyst, chiral ligand, reagents. It is noteworthy that this approach considerable advantages, such as excellent (>95:5 for >40 examples), stereo- (up to >95:5 E/Z), enantioselectivity (92-99% ee, >35 examples) control, mild reaction conditions, broad substrate scope, good functional group compatibility, making it a great improvement alkyne-aldehyde reactions.

Language: Английский

Citations

107

Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis DOI
Masakazu Nambo,

Yuuki Maekawa,

Cathleen M. Crudden

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 3013 - 3032

Published: Feb. 18, 2022

Sulfones are common, readily available reagents that have recently attracted attention as versatile for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design sulfonyl group is a critical factor control reactivity. The concepts presented herein will provide new strategies construct diverse molecules with high efficiency modularity.

Language: Английский

Citations

86

Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C–S bond functionalization of sulfones DOI Creative Commons
Javier Corpas, Shin‐Ho Kim‐Lee, Pablo Mauleón

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(15), P. 6774 - 6823

Published: Jan. 1, 2022

Sulfones are excellent candidates for the design of new C–C and C–X bond-forming reactions owing to easy activation C–S bonds. This review focuses on challenges recent opportunities catalytic functionalization sulfones.

Language: Английский

Citations

80

Photoinduced Cobalt-Catalyzed Desymmetrization of Dialdehydes to Access Axial Chirality DOI
Hao Jiang,

Xiang‐Kui He,

Xuan‐Feng Jiang

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(12), P. 6944 - 6952

Published: March 15, 2023

Enantioselective metallaphotoredox catalysis, which combines photoredox catalysis and asymmetric transition-metal has become an effective approach to achieve stereoconvergence under mild conditions. Although many impressive synthetic approaches have been developed access central chirality, the construction of axial chirality by still remains underexplored. Herein, we report two visible light-induced cobalt-catalyzed reductive couplings biaryl dialdehydes synthesize axially chiral aldehydes (60 examples, up 98% yield, >19:1 dr, >99% ee). This protocol shows good functional group tolerance, broad substrate scope, excellent diastereo- enantioselectivity.

Language: Английский

Citations

80