Ni-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to a-Amino Ketones DOI Creative Commons
Yang Gao, Phil S. Baran

Опубликована: Сен. 13, 2023

A new approach to the enantiocontrolled synthesis of alpha-amino ketone derivatives is disclosed by employing a decarboxylative acylation strategy. Thus, when an acyl chloride and alpha-amido-containing redox-active ester are exposed Ni-catalysis, chiral ligand, metal reductant, alpha-amido ketones produced in good yield high ee. The reaction exhibits broad substrate scope, can be easily scaled up, applied dramatically simplify several known structures.

Язык: Английский

Desymmetrization–Addition Reaction of Cyclopropenes to Imines via Synergistic Photoredox and Cobalt Catalysis DOI

Xiang‐Kui He,

Liang‐Qiu Lu,

Bao-Ru Yuan

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(28), С. 18892 - 18898

Опубликована: Июль 5, 2024

Herein, we designed a reaction for the desymmetrization-addition of cyclopropenes to imines by leveraging synergy between photoredox and asymmetric cobalt catalysis. This protocol facilitated synthesis series chiral functionalized cyclopropanes with high yield, enantioselectivity, diastereoselectivity (44 examples, up 93% yield >99% ee). A possible mechanism involving cyclopropene desymmetrization Co-H species imine addition Co-alkyl was proposed. study provides novel route important extends frontier metallaphotoredox

Язык: Английский

Процитировано

18

Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas DOI

Yetong Zhang,

Qihang Cao,

Yang Xi

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(12), С. 7971 - 7978

Опубликована: Март 14, 2024

We describe a nickel-catalyzed carbonylative cross-coupling of unactivated secondary alkyl electrophiles with the organozinc reagent at atmospheric CO gas, thus allowing expedient construction unsymmetric dialkyl ketones broad functional group tolerance. The leverage newly developed

Язык: Английский

Процитировано

17

Recent advances in dual photoredox/nickel catalyzed alkene carbofunctionalised reactions DOI

Anilkumar Kommoju,

Kattamuri Snehita,

K. Sowjanya

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(68), С. 8946 - 8977

Опубликована: Янв. 1, 2024

Alkene carbofunctionalization reactions have great potential for synthesizing complex molecules and constructing structures in natural products medicinal chemistry. Recently, dual photoredox/nickel catalysis has emerged as a novel strategy alkene carbofunctionalization. Nickel offers numerous advantages over other transition metals, such cost-effectiveness, abundance, low toxicity, moreover, it many oxidation states. catalysts exhibit excellent catalytic activity photoredox/transition metal catalysis, facilitating the formation of carbon-carbon or carbon-heteroatom bonds organic transformations. This review highlights latest advancements photoredox/nickel-catalyzed carbofunctionalizations includes literature published from 2020 to 2024.

Язык: Английский

Процитировано

9

Nickel‐Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α‐Amino Ketones** DOI Creative Commons
Yang Gao, Phil S. Baran

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(50)

Опубликована: Ноя. 8, 2023

A new approach to the enantiocontrolled synthesis of α-amino ketone derivatives is disclosed by employing a decarboxylative acylation strategy. Thus, when an acyl chloride and α-amido-containing redox-active ester are exposed nickel catalyst, chiral ligand, metal reductant, α-amido ketones produced in good yield high ee. The reaction exhibits broad substrate scope, can be easily scaled up, applied dramatically simplify several known structures.

Язык: Английский

Процитировано

15

Cu-Catalyzed Asymmetric Three-Component Radical Acylarylation of Vinylarenes with Aldehydes and Aryl Boronic Acids DOI
Zhiheng Li, Shang Wang, Si‐Cong Chen

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(47), С. 32235 - 32242

Опубликована: Ноя. 13, 2024

The direct use of readily available aldehydes as acyl radical precursors has facilitated diverse three-component acylative difunctionalization reactions alkenes, offering a powerful route to synthesize β-branched ketones. However, asymmetric alkenes with still remains elusive. Here we report copper-catalyzed acylarylation vinylarenes and aryl boronic acids. This method begins formation from an aldehyde via hydrogen atom transfer. adds the alkene, forming new benzylic that then undergoes enantioselective arylation. A chiral binaphthyl-tethered bisoxazoline ligand is essential for achieving high stereocontrol. strategy enables synthesis range synthetically valuable β,β-diaryl ketones vinylarenes.

Язык: Английский

Процитировано

3

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO DOI
Chenglong Wang, Ning Liu, Xianqing Wu

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(6), С. 599 - 604

Опубликована: Ноя. 2, 2023

Comprehensive Summary Transition metal‐catalyzed carbometallation of unsaturated hydrocarbons constitutes one the most efficient synthetic methodologies for construction C—C bond. Recently, incorporation organometallic reagent with CO gas as a nucleophilic acyl synthon could enable acylmetallation reaction, which greatly increases horizon chemistry. Herein, we report nickel‐catalyzed regiodivergent acylzincation o ‐cyano cinnamate ester and styrene, in cyano moiety intramolecularly captures zinc intermediates to trigger tandem cyclization process. This protocol features mild conditions, broad substrate scope excellent functional group tolerance, thus affording diverse array highly functionalized carbocyclic compounds.

Язык: Английский

Процитировано

7

Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene DOI Open Access
Licheng Wu, Xianqing Wu, Jingping Qü

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(12), С. 4239 - 4239

Опубликована: Янв. 1, 2023

Язык: Английский

Процитировано

5

Nickel/Titanocene-Catalyzed Electrophilic Acylation Coupling of Styrene Oxides DOI
Jincan Li,

Chang Cao,

Haihong Wu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 6959 - 6963

Опубликована: Сен. 20, 2023

The cross-coupling of epoxides with acyl chlorides or anhydrides by a nickel/titanocene dual catalytic system is established. A variety synthetically useful β-hydroxy ketones were obtained in good to high yields using modified pyridine-oxazoline ligand. reaction proceeds via the cooperation titanocene-catalyzed ring-opening and nickel-catalyzed acylation benzylic radical intermediate.

Язык: Английский

Процитировано

3

Nickel‐Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α‐Amino Ketones** DOI Creative Commons
Yang Gao, Phil S. Baran

Angewandte Chemie, Год журнала: 2023, Номер 135(50)

Опубликована: Ноя. 8, 2023

Abstract A new approach to the enantiocontrolled synthesis of α‐amino ketone derivatives is disclosed by employing a decarboxylative acylation strategy. Thus, when an acyl chloride and α‐amido‐containing redox‐active ester are exposed nickel catalyst, chiral ligand, metal reductant, α‐amido ketones produced in good yield high ee. The reaction exhibits broad substrate scope, can be easily scaled up, applied dramatically simplify several known structures.

Язык: Английский

Процитировано

0

Ni-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to a-Amino Ketones DOI Creative Commons
Yang Gao, Phil S. Baran

Опубликована: Сен. 13, 2023

A new approach to the enantiocontrolled synthesis of alpha-amino ketone derivatives is disclosed by employing a decarboxylative acylation strategy. Thus, when an acyl chloride and alpha-amido-containing redox-active ester are exposed Ni-catalysis, chiral ligand, metal reductant, alpha-amido ketones produced in good yield high ee. The reaction exhibits broad substrate scope, can be easily scaled up, applied dramatically simplify several known structures.

Язык: Английский

Процитировано

0