Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis

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

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Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances

Synthesis, Год журнала: 2023, Номер 55(20), С. 3239 - 3250

Опубликована: Апрель 26, 2023

Abstract The ubiquity of carboxylic acids as naturally derived or man-made chemical feedstocks has spurred the development powerful, decarboxylative C–C bond-forming transformations for organic synthesis. Carboxylic benefit not only from extensive commercial availability, but are stable surrogates organohalides organometallic reagents in transition-metal-catalysed cross-coupling. Open shell reactivity (or derivatives thereof) to furnish carbon-centred radicals is proving transformative synthetic chemistry, enabling novel and strategy-level C(sp3)–C bond disconnections with exquisite chemoselectivity. This short review will summarise several latest advances this ever-expanding area. 1 Introduction 2 Improved Decarboxylative Arylations 3 sp3–sp3 Cross-Coupling Acids Aliphatic Bromides 4 Alcohols Amines 5 Doubly 6 Bond Formation (Hetero)aryl 7 Conclusions

Язык: Английский

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The Multiple Roles of Bipyridine-Nickel(II) Complex in Versatile Photoredox C(sp²)–C(sp³) Cross-Coupling

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 3328 - 3338

Опубликована: Фев. 9, 2025

Язык: Английский

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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

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

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Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1H)-ones via Electron Donor–Acceptor Complexes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13339 - 13350

Опубликована: Авг. 31, 2023

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation photoactivated electron donor–acceptor complex between present method provides mild environmentally friendly protocol that exhibits good atom economy excellent functional group tolerance to obtain library biologically significant α-aminomethylated in yields.

Язык: Английский

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Alkyl Azetidines Via Batch and Flow Photochemistry

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 4, 2025

Alkyl azetidines have been prepared by photochemical modifications of azetidine-2-carboxylic acids in batch and flow. The reaction has realized milligram, gram, even multigram quantities. obtained are valuable building blocks for drug discovery.

Язык: Английский

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Kilo-Scale-Enabled Route toward PF-07907063, a Type II Brain Penetrant cMET Inhibitor

Organic Process Research & Development, Год журнала: 2025, Номер unknown

Опубликована: Апрель 7, 2025

Язык: Английский

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An overview of the synthesis of biheterocyclic compounds featuring four-membered rings containing nitrogen, oxygen, or sulfur

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134679 - 134679

Опубликована: Апрель 1, 2025

Язык: Английский

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Visible‐Light Mediated C‐3 Amination of Quinoxalin‐ 2(1H)‐ones via Electron Donor‐Acceptor Complexation

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(8)

Опубликована: Май 22, 2024

Abstract The formation of carbon‐nitrogen bonds holds paramount importance in the realm synthetic organic chemistry, finding extensive applications synthesis pharmaceuticals, agrochemicals, and materials. Herein, we describe a novel EDA complex mediated, metal‐ photocatalyst‐free, visible‐light‐initiated direct C‐3 amination biologically important, quinoxalin‐2(1 H )‐one moiety. key to success lies photoactivated electron donor‐acceptor between amine, which undergo subsequent transfer reaction effect desired transformation. A diverse array 3‐aminoquinoxalin‐2(1 )‐ones were prepared employing this process yields are up 87%. This work represents significant advancement toward more environmentally friendly efficient approach, characterized by mild conditions high atom economy.

Язык: Английский

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Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

ChemistrySelect, Год журнала: 2024, Номер 9(20)

Опубликована: Май 22, 2024

Abstract Decarboxylative cross‐coupling is a significant method in organic synthesis where inexpensive and stable carboxylic acids are used as substrates for the construction of C−C C‐heteroatom bonds. First‐row 3d transition metals including nickel have recently been recognized advantageous alternative to noble metal catalysed decarboxylative couplings. In this review, Ni‐based catalysts (C sp3 /C sp2 /Csp) (C−N, C−P, C−S, C−Si) cross‐couplings summarized most strategies find applications modification biologically important molecules. Importantly, Ni‐dual catalysis under photocatalytic electrochemical conditions form state art research field. This first review reported exclusively on Ni‐catalysed cover reports from 2009 present.

Язык: Английский

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