Ni-Catalyzed Enantioselective Three-Component Reductive Alkylacylation of Enamides DOI Creative Commons
Jichao Xiao,

Tingting Jia,

Shuang Chen

и другие.

Опубликована: Июнь 21, 2024

Chiral alpha-amino ketones have found extensive applications as functional molecules. A nickel-catalyzed, enantioselective, and fully intermolecular three-component 1,2-alkylacylation of N-acyl enamides has been realized with tertiary alkyl bromides carboxylic acid-derived electrophiles the coupling reagents. This reductive strategy is operationally simple, exhibiting broad substrate scope excellent group tolerance using readily available starting materials allowing rapid access to structurally complex α-amino ketone derivatives in high enantioselectivity. suitable chiral biimidazoline ligand together additional chelation amide carbonyl a Ni intermediate facilitates enantioselective control by suppressing background reaction, accounting for Mechanistic studies indicated intermediacy radical species.

Язык: Английский

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4488 - 4515

Опубликована: Янв. 1, 2023

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

Язык: Английский

Процитировано

31

A general electron donor–acceptor complex enabled cascade cyclization of alkynes to access sulfur-containing heterocycles DOI
Wenchao Yang, Yu Sun, Xiaobo Bao

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(8), С. 3111 - 3116

Опубликована: Янв. 1, 2023

A general visible light-promoted and electron–donor–acceptor complex-enabled cascade reaction of alkynes to produce functionalized sulfur-containing heterocycles under photocatalyst-, base-, oxidant- metal-free conditions was developed.

Язык: Английский

Процитировано

28

Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent DOI
Jiaxuan Shen, Jincan Li, Meijun Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(5), С. 1166 - 1172

Опубликована: Янв. 1, 2023

Visible light-induced intermolecular thiolation/pyridylation of styrenes using a thiolate-based EDA complex as bifunctional reagent under mild conditions free photocatalyst, metal or external redox agent is reported.

Язык: Английский

Процитировано

26

Recent Advances in Nonprecious Metal Catalysis DOI
Michael C. Haibach, Shashank Shekhar, Tonia S. Ahmed

и другие.

Organic Process Research & Development, Год журнала: 2023, Номер 27(3), С. 423 - 447

Опубликована: Фев. 17, 2023

Nonprecious-metal-catalyzed alternatives to powerful precious metal transformations are of increasing interest in academia and the pharmaceutical industry due lower cost, better sustainability, toxicity. With continual growth broad field nonprecious catalysis (NPMC), we have chosen highlight selected articles published from March June 2022 which intended examples NPMC that feel may be especially relevant development. We aim inspire academic industrial innovation through discussion herein.

Язык: Английский

Процитировано

23

Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis DOI Creative Commons
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest

и другие.

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Язык: Английский

Процитировано

12

Ligand-Controlled Regioreversed 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Photoredox/Nickel Catalysis DOI
Ye Fu,

Songlin Zheng,

Yixin Luo

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(11), С. 8505 - 8517

Опубликована: Май 16, 2024

A ligand-controlled regioreversed 1,2-arylalkylation of alkenes via photoredox/nickel dual catalysis is reported. In contrast with previous reports on photoredox/nickel-catalyzed 1,2-alkylarylation reactions that initiate from the Giese addition an alkyl radical to alkene, this three-component conjugate coupling process occurs through nickel-catalyzed aryl thereby leading a complementary regioselectivity conventional 1,2-alkylarylation. An ortho-substituted bipyridyl ligand key tune regioselectivity, which was found be dictated by reactivity alkene-coordinated LnNi(0) complexes trigger formation radicals halogen-atom transfer (XAT). This transformation allows concise entry structurally abundant β-amino acid derivatives, including ORL1-receptor antagonists.

Язык: Английский

Процитировано

10

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

8

Visible‐Light‐Promoted Electron Donor‐Acceptor Complex Enabled Decarboxylative Alkylation of Quinoxalin‐2(1H)‐ones and N‐Hydroxyphthalimide Esters with Na2S as a Catalytic Donor DOI

Hai‐Yang Song,

Zhuo‐Tao Zhang,

Hong‐Yu Tan

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(2)

Опубликована: Янв. 11, 2023

Abstract We developed a novel and efficient method for the synthesis of various 3‐alkylated quinoxalin‐2(1 H )‐ones (32 examples, 70%–96% yields) through electron donor‐acceptor complex enabled alkylation with N ‐ hydroxyphthalimide esters as alkyl source Na 2 S catalytic donor under external photocatalyst‐, oxidant‐ additive‐free conditions.

Язык: Английский

Процитировано

22

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 1056 - 1085

Опубликована: Янв. 1, 2023

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

Язык: Английский

Процитировано

20

Three-component reductive conjugate addition/aldol tandem reaction enabled by nickel/photoredox dual catalysis DOI Creative Commons
Hongping Zhao, Weiming Yuan

Chemical Science, Год журнала: 2023, Номер 14(6), С. 1485 - 1490

Опубликована: Янв. 1, 2023

A three-component reductive cross-coupling of aryl halides, aldehydes, and alkenes by nickel/photoredox dual catalysis is disclosed. The key to success for this tandem transformation identify α-silylamine as a unique organic reductant, which releases silylium ions instead protons prevent unwanted protonation processes, meanwhile serves Lewis acid activate aldehydes in situ. This catalytic protocol completes traditional conjugate addition/aldol sequence that eliminates the requirement organometallic reagents metal-based reductants, thus providing mild synthetic route highly valuable β-hydroxyl carbonyl compounds with contiguous 1,2-stereocenters.

Язык: Английский

Процитировано

19