Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI
Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Recent advances in combining photo- and N-heterocyclic carbene catalysis DOI Creative Commons
Xiaochen Wang,

Senhui Wu,

Rongxin Yang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(46), P. 13367 - 13383

Published: Jan. 1, 2023

This review summarizes recent advances in combining photo- and N-heterocyclic carbene catalysis, as well provides an outlook on future opportunities challenges.

Language: Английский

Citations

43

Radical Reactions with N-Heterocyclic Carbene (NHC)-Derived Acyl Azoliums for Access to Multifunctionalized Ketones DOI

Hui Cai,

Xiaoqun Yang,

Shi‐Chao Ren

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8270 - 8293

Published: May 13, 2024

As one of the most important key intermediates, NHC-bound acylazolium-based ionic transformations have been intensively explored in past two decades. With expeditious development NHC-catalyzed radical recent years, acylazolium chemistry has reached another level, with number relevant publications increasing significantly. However, a summary focused on acylations NHC-derived acyl azoliums classified according to mechanistic difference not reported. Such detailed classification and deep analysis provide opportunities for better understanding history trend this field. In review, reactions N-heterocyclic carbene (NHC)-derived are systematically introduced. The achievements challenges within area also summarized discussed at end.

Language: Английский

Citations

23

Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds DOI
Jiaqiong Sun, Lihong V. Wang, Guangfan Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4488 - 4515

Published: Jan. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Language: Английский

Citations

31

Synthesis of axially chiral diaryl ethers via NHC-catalyzed atroposelective esterification DOI Creative Commons

Yingtao Wu,

Xin Guan,

Huaqiu Zhao

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(12), P. 4564 - 4570

Published: Jan. 1, 2024

We present NHC-catalyzed atroposelective esterification of prochiral dialdehydes, delivering enantioenriched axially chiral diaryl ethers. Matched kinetic resolutions amplify the enantioselectivity by removing minor enantiomers via over-functionalization.

Language: Английский

Citations

15

Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis DOI

Wan-Cong Liu,

Xiang Zhang, Lin Chen

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3181 - 3190

Published: Feb. 14, 2024

Cross-coupling reactions have been well received as one of the most popular protocols for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they rarely utilized radical precursors acylative reactions. Herein, we reported energy-transfer-enabled acylation using free via NHC/photo dual catalysis. This protocol could efficiently promote Suzuki-type cross-coupling between acyl imidazoles multicomponent alkylacylations alkenes, thus producing various ketones with structural diversity. Additionally, products can readily transform into a large number structurally interesting fine chemicals. Preliminary mechanistic studies shed light on unique reaction mechanism.

Language: Английский

Citations

10

Copper‐Catalyzed 1,2‐Dicarbonylative Cyclization of Alkenes with Alkyl Bromides via Radical Cascade Process DOI Creative Commons
Fengqian Zhao,

Xing‐Wei Gu,

Robert Franke

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(49)

Published: Oct. 18, 2022

Herein, we developed a new procedure on 1,2-dicarbonylative cyclization of 4-aryl-1-butenes with alkyl bromides. Using simple copper catalyst, two molecules carbon monoxide were introduced into the double bond formation four C-C bonds and ring. Various α-tetralones 2,3-dihydroquinolin-4-ones formed in moderate to good yields.

Language: Английский

Citations

29

Radical acylation: concepts, synthetic applications and directions DOI
Yue Zhang, Yili Zhang, Jian Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1056 - 1085

Published: Jan. 1, 2023

In this tutorial, reaction scopes, limitations and mechanisms of radical acylations are summarized discussed according to types catalytic systems.

Language: Английский

Citations

20

Visible Light‐Mediated Cobalt and Photoredox Dual‐Catalyzed Asymmetric Reductive Coupling for Axially Chiral Secondary Alcohols DOI

Tianlong Liang,

Yingtao Wu,

Jiaqiong Sun

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(23), P. 3253 - 3260

Published: July 20, 2023

Comprehensive Summary Secondary alcohols bearing both axial and central chirality comprise attractive biological activity exhibit excellent chiral induction in asymmetric reactions. However, only very limited catalytic approaches were developed for their synthesis. We herein describe visible light‐mediated cobalt‐catalyzed reductive Grignard‐type addition of aryl iodides with axially prochiral biaryl dialdehydes leading to the direct construction secondary alcohols. Preliminary mechanistic studies indicate that efficient kinetic recognition diastereomers might occur improve stereoselectivity, which open a new avenue challenging cascade multiple elements. This protocol features enantio‐ diastereoselectivity, green mild conditions, simple operation, broad substrate scope, providing modular platform synthesis

Language: Английский

Citations

19

Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenesviaacyl and allyl radical cross-coupling DOI
Lihong V. Wang, Jiaqiong Sun,

Jiuli Xia

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1047 - 1055

Published: Jan. 1, 2023

Visible light-mediated NHC and photoredox co-catalyzed radical 1,2-sulfonylacylation of allenes via cross-coupling between an allyl NHC-stabilized acyl radical.

Language: Английский

Citations

17

Recent Advances in Base‐Metal‐Catalyzed Carbonylation of Unactivated Alkyl Electrophiles DOI
Wei Li,

Donghao Jiang,

Cheng Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(23), P. 3419 - 3432

Published: July 27, 2023

Comprehensive Summary Transition metal‐catalyzed carbonylation reactions represent a direct and atom‐economical approach to synthesize carbonyl compounds or their derivatives by using CO as cheap readily available C1 feedstock. While of C(sp 2 )‐hybridized electrophiles ( e.g ., aryl halides) is well developed, less reactive unactivated alkyl remains challenging. Recently, the use earth‐abundant base metals including Cu, Co, Mn, Fe, Ni catalysts has enabled advances in carbonylative coupling for approaching diverse derivatives, notably, some which are synthetic importance but difficult be synthesized through previous reported methods. Herein, we have summarized discussed these recent achievements base‐metal‐catalyzed C—C, C—N, C—O, C—X other source.

Language: Английский

Citations

17