Directing group migration strategy in transition-metal-catalysed direct C–H functionalization

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(6), P. 3677 - 3689

Published: Jan. 1, 2021

In this tutorial review, the rapid advances of directing group (DG) migration in transition-metal-catalysed direct C–H activation was presented through analyzing and comparing different bond cleavage trigger DG (including N–O, N–C, N–N or O–C).

Language: Английский

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Advances in 2H-azirine chemistry: A seven-year update

Tetrahedron, Journal Year: 2019, Volume and Issue: 75(18), P. 2555 - 2624

Published: March 28, 2019

Language: Английский

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Transition Metal Promoted Cascade Heterocycle Synthesis through C−H Functionalization

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(44), P. 9749 - 9783

Published: June 18, 2020

Sequential, domino and tandem reactions could be defined as a sequence of synthetic transformations that occur one after the other, in same reaction flask. This Review highlights recent advances at overlap two worlds: transition-metal mediated C-H activation trigger cascade reaction, for heterocycles synthesis. To shed some light on this intricate "middle-earth", focus was put mechanism rather than type metal or chronological order reaction. The aim is to separate, then highlight, true initiated by activation, compared other examples functionalization heterocycle syntheses.

Language: Английский

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gem ‐Difluoromethylene Alkyne‐Enabled Diverse C−H Functionalization and Application to the on‐DNA Synthesis of Difluorinated Isocoumarins

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(4), P. 1959 - 1966

Published: Oct. 6, 2020

Using gem-difluoromethylene alkynes as effectors, unprecedented diverse C-H activation/[4+2] annulations of simple benzoic acids are reported. The chemodivergent reaction outcomes well-tuned by Rh/Ir-catalyzed system; in the RhIII catalysis, 3-alkenyl-1H-isochromen-1-one and 3,4-dialkylideneisochroman-1-one skeletons afforded a solvent-dependent manner whereas difluoromethylene-substituted 1H-isochromen-1-ones generated under IrIII -catalyzed system. Mechanistic studies revealed that unusually double β-F eliminations fluorine effect-induced regioselective reductive elimination independently involved to enable distinct modes for divergent product formations. Besides, synthetic application both derivatization obtained diene products on-DNA synthesis DNA-tagged difluorinated isocoumarin have been demonstrated, which manifested great potential utility developed protocols.

Language: Английский

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Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen‐, Carbon‐, Oxygen‐, Boron‐, Silicon‐, Phosphorus‐, and Sulfur‐Containing Nucleophiles

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(21), P. 4839 - 4881

Published: July 4, 2019

Abstract Ynones are widely used in organic synthesis. Their great success is rooted their multiple functional groups. This review focus on advance of ynones published the decade 2009–2019. Reactions triggered by conjugate addition nitrogen‐, carbon‐, oxygen‐, boron‐, silicon‐, phosphorus‐, and sulfur‐containing nucleophiles thoroughly discussed summarized herein. Multicomponent reactions, rearrangements, cycloadditions, regio‐ stereoselective synthesis, oxidations, coupling, green chemistry et al. depicted detail. We hope that this will promote future research area. magnified image

Language: Английский

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Intermolecular Redox-Neutral Carboamination of C–C Multiple Bonds Initiated by Transition-Metal-Catalyzed C–H Activation

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(23), P. 14754 - 14772

Published: Nov. 18, 2022

Carboamination of readily available feedstock-like alkenes, alkynes, and allenes has proven to be an efficient powerful tool for the synthesis diverse valuable amine derivatives relevance medicinal chemistry, biochemistry, material science. Among these developed carboamination methodologies, direct use C–H activation strategy leverage process is particularly attractive due ubiquity such bonds in organic molecules. In this review, we provide overview development intermolecular across C–C π-bonds initiated by a redox-neutral nonannulative manner, with emphasis on synthetic mechanistic aspects. principle, review summarized reactions key feature involving initial metalation followed migratory insertion into terminated electrophilic amination quenching, thus, it ordered sources C- N-based functionalities further divided π-compounds.

Language: Английский

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Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C–H/C–C Activations

Organic Letters, Journal Year: 2019, Volume and Issue: 21(8), P. 2823 - 2827

Published: March 27, 2019

A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C–H/C–C activations using internal oxidative O–NHAc −OH as the dual directing groups has been achieved. This reaction provided an efficient regioselective approach to benzofuran derivatives good functional group compatibility high yields.

Language: Английский

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Remote C6-Enantioselective C–H Functionalization of 2,3-Disubstituted Indoles through the Dual H-Bonds and π–π Interaction Strategy Enabled by CPAs

Organic Letters, Journal Year: 2019, Volume and Issue: 21(21), P. 8662 - 8666

Published: Oct. 22, 2019

A versatile dual H-bonds and π–π interaction strategy that enables enantioselective remote C6-selective C–H functionalization of 2,3-disubstituted indoles was first reported. The N–H bond indole pivotal to achieve the C6 with excellent yield enantioselectivity. Furthermore, this methodology leads efficient construction numerous enantioenriched C6-functionalized products under mild reaction conditions employing different electrophiles. Preliminary cell proliferation investigations revealed synthesized chiral C6-substituted derivatives had potential anticancer activities.

Language: Английский

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Cobalt-Catalyzed Ortho-C(sp²)–H Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Groups

Organic Letters, Journal Year: 2019, Volume and Issue: 21(18), P. 7342 - 7345

Published: Sept. 3, 2019

An efficient and convenient cobalt-catalyzed ortho-C(sp2)–H amidation of benzaldehydes employing dioxazolones as the aminating reagent has been developed. The key feature this protocol is use green economic earth-abundant metals cobalt catalyst with p-chloroaniline transient directing group. Further application our approach was demonstrated by synthesis C1r serine protease inhibitor 45 elastase 49.

Language: Английский

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Recent Advances in Catalytic Enantioselective Synthesis of Fluorinated α‐ and β‐Amino Acids

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(22), P. 4763 - 4793

Published: Sept. 23, 2020

Abstract Enantioenriched fluorinated α‐ and β‐amino acids are often encountered in numerous pharmaceuticals bioactive molecules, also of great importance as probes PET NMR for studying the behavior enzymes incorporation into peptides drug candidates. Among various synthetic strategies developed, catalytic enantioselective synthesis proves to be one most facile powerful protocols construct such privileged structures. The past decade has witnessed considerable progress construction chiral acid derivatives with structural diversity. In this review, we summarize these impressive achievements according bond‐forming way or acids, respectively, underline remaining challenges. This information would provide important guidance some inspiration researchers engaged organic fluorine medicinal chemistry. magnified image

Language: Английский

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