Ni-Catalyzed Reductive 1,2-Alkylarylation of Alkenes for the Synthesis of Spirocyclic γ-Lactams DOI

James W. Pearson,

Teh Ren Hou,

Jelena Golijanin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5560 - 5565

Published: June 25, 2024

An intermolecular nickel-catalyzed reductive 1,2-alkylarylation of acrylates with cyclopropylamine NHP esters and aryl iodides is reported. This operationally simple protocol provides direct access to 1-alkylcyclopropylamine scaffolds. The mild conditions are compatible four-membered α-amino strained rings as well five- six-membered ring systems. products undergo cyclization α-arylated spirocyclic γ-lactams─a motif present in several pharmaceuticals.

Language: Английский

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

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 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

Language: Английский

Citations

24

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

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

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3111 - 3116

Published: Jan. 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.

Language: Английский

Citations

30

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

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1166 - 1172

Published: Jan. 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.

Language: Английский

Citations

26

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

Songlin Zheng,

Yixin Luo

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8505 - 8517

Published: May 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.

Language: Английский

Citations

11

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

24

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

et al.

Organic Process Research & Development, Journal Year: 2023, Volume and Issue: 27(3), P. 423 - 447

Published: Feb. 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.

Language: Английский

Citations

23

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

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(2)

Published: Jan. 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.

Language: Английский

Citations

22

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

Chemical Science, Journal Year: 2023, Volume and Issue: 14(6), P. 1485 - 1490

Published: Jan. 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.

Language: Английский

Citations

19

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

Anilkumar Kommoju,

Kattamuri Snehita,

K. Sowjanya

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(68), P. 8946 - 8977

Published: Jan. 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.

Language: Английский

Citations

9