NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation DOI Open Access
Yousuke Yamaoka, Hideto Miyabe

Catalysts, Journal Year: 2024, Volume and Issue: 14(4), P. 219 - 219

Published: March 22, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) have opened new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C–O bond formation based on activation aldehyde C(sp2)–H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst also described.

Language: Английский

C(sp<sup>3</sup>)‐H Functionalization Using Chlorine Radicals DOI
Masoud Sadeghi

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2898 - 2918

Published: May 18, 2024

Abstract Converting any desired C−H bond to the intended C−Z in a given organic molecule could be final peak of functionalization methodology. Among three types bonds, ubiquitous C( sp 3 )−H has gained particular attention, especially last two decades. There are different ways transform bonds into bonds. The use chlorine radicals is one these methods with promising future. literature review shows that sources have been used for chlorine, including chloride ions (HCl or salts), coordinated chlorides (transition metal complexes), and (organochlorine compounds). However, HCl FeCl most attention among sources. major convert from radicals: 1) oxidation hydrogen salts, 2) photolysis chloride, 3) transition insertion C−Cl This summarizes published research papers on functionalization. Therefore, chlorination reactions which do not play direct role cleavage within scope this review.

Language: Английский

Citations

8

Asymmetric Dearomatization of Indoles through Cobalt‐Catalyzed Enantioselective C−H Functionalization Enabled by Photocatalysis DOI

Ming‐Ya Teng,

De‐Yang Liu,

Shi-Yu Mao

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: June 20, 2024

Photocatalysis holds a pivotal position in modern organic synthesis, capable of inducing novel reactivities under mild and environmentally friendly reaction conditions. However, the merger photocatalysis transition-metal-catalyzed asymmetric C-H activation as an efficient sustainable method for construction chiral molecules remains elusive challenging. Herein, we develop cobalt-catalyzed enantioselective enabled by visible-light photoredox catalysis, providing synergistic catalytic strategy dearomatization indoles with high levels enantioselectivity (96 % to >99 ee). Mechanistic studies indicate that excited photocatalyst was quenched divalent cobalt species presence Salox ligand, leading formation catalytically active Co(III) complex. Moreover, stoichiometric reactions cobaltacycle intermediate indole suggest irradiation visible light also play critical role step.

Language: Английский

Citations

8

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate DOI Creative Commons

Zongbin Jia,

Liang Cheng, Long Zhang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 14, 2024

Abstract The direct alkenylation with simple alkenes stands out as the most ideal yet challenging strategy for obtaining high-valued desaturated alkanes. Here we present a asymmetric dehydrogenative α -C(sp 3 )-H of carbonyls based on synergistic photoredox-cobalt-chiral primary amine catalysis under visible light. ternary catalytic system enables coupling β -keto-carbonyls and through cooperative radical addition-dehydrogenation process involving chiral -imino Co(II)-metalloradical intermediate. A H-transfer nitrobenzene is engaged to quench in situ generated cobalt hydride species, ensuring chemoselective good yields high enantioselectivities.

Language: Английский

Citations

5

Advances in photochemical/electrochemical synthesis of heterocyclic compounds from carbon dioxide DOI
Yuyang Xie, Ying‐Ming Pan

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This paper reviews progress in the photochemical/electrochemical construction of heterocyclic compounds using CO 2 , differentiating between various reaction types and elucidating their underlying mechanisms as well potential applications.

Language: Английский

Citations

5

Catalytic asymmetric oxidative coupling between C(sp3)–H bonds and carboxylic acids DOI Creative Commons
Xianming Liu, Fu Li,

Tongkun Wang

et al.

Published: Aug. 13, 2024

Direct enantioselective functionalization of C(sp3)–H bonds in organic molecules could fundamentally transform the synthesis chiral molecules. In particular, oxidation these would dramatically change production alcohols and esters, which are prevalent natural products, pharmaceuticals, fine chemicals. Remarkable advances have been made construction carbon-carbon carbon-nitrogen through bond functionalization. However, direct formation carbon-oxygen from remains a considerable challenge. We herein report highly oxidative coupling with carboxylic acids using molecular copper catalyst activated by blue light. The method applies to allylic propargyl C–H more importantly employs various as oxygenating agents. By this method, we successfully synthesized range esters directly readily available alkenes alkynes, greatly simplifying related alcohols.

Language: Английский

Citations

5

Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates DOI Creative Commons
Yu Guo,

Guotao Lin,

Mengjie Zhang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 25, 2024

Due to the high reactivity and versatility of benzenesulfonothioates, significant advancements have been made in constructing C-S bonds. However, there are certain limitations synthesis S-thiosulfonates SS-thiosulfonates, especially when dealing with substantial steric hindrance, which poses a challenge. Herein, we present an innovative approach for assembling unsymmetric SS-thiosulfonates through integration dual copper/photoredox catalysis. Moreover, also realized one-pot strategy by directly using carboxylic acids as raw materials in-situ activation them access without further purification presynthesis NHPI esters. The envisaged utilization these reagents poised pioneer pathway fabricating versatile spectrum mono-, di-, polysulfide compounds. Furthermore, they introduce class potent sulfenylating reagents, empowering intricate unsymmetrical disulfides that were previously challenging access. conventional method synthesizing thioether compounds typically relies on thiol, disulfide, sulfinyl halide initial substances, suffering from strong odors, limited availability, issues. Here, authors catalysis

Language: Английский

Citations

5

Radical-polar Crossover Reaction of Glycine Derivatives DOI

Youwan Ye,

Xin Zhang,

Peng Kong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10378 - 10381

Published: Jan. 1, 2024

Here we report a visible-light facilitated radical addition strategy for the preparation of various natural or unnatural α-amino acids from readily available glycine derivatives and alkenes. A key aspect in achieving this side carbon chain introduction reaction, while circumventing well-documented cyclization pathway, was employment radical-polar crossover under redox neutral conditions.

Language: Английский

Citations

5

Recent progress in visible light‐driven halogenation: Chlorination, bromination, and iodination DOI

Anh Thu Nguyen,

Houng Kang, Truong Giang Luu

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2024, Volume and Issue: 45(9), P. 738 - 758

Published: Sept. 1, 2024

Abstract Halogenation is one of the most important transformations in organic synthesis. Halogenated compounds are employed many reactions to prepare useful molecules. Many methods have been developed introduce halogens into different compounds. Visible light‐mediated efficient, low‐toxic, and mild‐condition applied for various chemistry transformations. Remarkably, there has an increasing development application visible light‐induced halogenation recent years. Herein, we present a comprehensive summary including chlorination, bromination, iodination under light irradiation since 2020.

Language: Английский

Citations

5

Ni-Catalyzed Deoxygenative Cross-Coupling of Alcohols with Aryl Chlorides via an Organic Photoredox Process DOI

Weikang Xiong,

Tengfei Kang, Fei Li

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14089 - 14097

Published: Sept. 10, 2024

Language: Английский

Citations

5

Alkylation of Glycine Derivatives through a Synergistic Single-Electron Transfer and Halogen-Atom Transfer Process DOI

Peng Kong,

Youwan Ye,

Xin Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7507 - 7513

Published: Aug. 29, 2024

Here, we present a versatile method for forming C(sp

Language: Английский

Citations

4