Electrochemically driven cross-electrophile coupling of alkyl halides

Nature, Journal Year: 2022, Volume and Issue: 604(7905), P. 292 - 297

Published: Feb. 21, 2022

Language: Английский

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An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates

Nature Chemistry, Journal Year: 2021, Volume and Issue: 13(10), P. 950 - 955

Published: Sept. 28, 2021

Language: Английский

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Exploiting the sp2 character of bicyclo[1.1.1]pentyl radicals in the transition-metal-free multi-component difunctionalization of [1.1.1]propellane

Nature Chemistry, Journal Year: 2022, Volume and Issue: 14(9), P. 1068 - 1077

Published: July 21, 2022

Language: Английский

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Dicarbofunctionalization of [1.1.1]Propellane Enabled by Nickel/Photoredox Dual Catalysis: One-Step Multicomponent Strategy for the Synthesis of BCP-Aryl Derivatives

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(28), P. 12961 - 12969

Published: July 6, 2022

Bicyclo[1.1.1]pentane (BCP) motifs as para-disubstituted aryl bioisosteres are playing an emerging role in pharmaceutical, agrochemical, and materials chemistry. The vast majority of these structures is obtained from a BCP electrophile or nucleophile, which themselves derived [1.1.1]propellane via cleavage the internal C–C bond through addition either radicals metal-based nucleophiles. Compared with current stepwise approaches, multicomponent reaction that provides direct access to complex diverse disubstituted products would be more attractive. Herein, we report single-step, approach synthetically versatile arylated nickel/photoredox catalysis. Importantly, this three-component process allows two bonds formed single step sets three quaternary centers, unprecedented any previously reported methods. method has been demonstrated allow architectures halide radical precursor substrates.

Language: Английский

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2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring

Nature Chemistry, Journal Year: 2023, Volume and Issue: 15(8), P. 1155 - 1163

Published: June 5, 2023

Abstract The ortho -substituted phenyl ring is a basic structural element in chemistry. It found more than three hundred drugs and agrochemicals. During the past decade, scientists have tried to replace bioactive compounds with saturated bioisosteres obtain novel patentable structures. However, most of research this area has been devoted replacement para ring. Here we developed improved physicochemical properties: 2-oxabicyclo[2.1.1]hexanes. Crystallographic analysis revealed that these structures indeed similar geometric properties. Replacement marketed agrochemicals fluxapyroxad (BASF) boscalid 2-oxabicyclo[2.1.1]hexanes dramatically their water solubility, reduced lipophilicity importantly retained bioactivity. This work suggests an opportunity for chemists medicinal chemistry agrochemistry.

Language: Английский

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Catalytic undirected borylation of tertiary C–H bonds in bicyclo[1.1.1]pentanes and bicyclo[2.1.1]hexanes

Nature Chemistry, Journal Year: 2023, Volume and Issue: 15(5), P. 685 - 693

Published: March 27, 2023

Language: Английский

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Three-dimensional saturated C(sp3)-rich bioisosteres for benzene

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(8), P. 605 - 627

Published: July 9, 2024

Language: Английский

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Terminal C(sp ³ )–H borylation through intermolecular radical sampling

Science, Journal Year: 2024, Volume and Issue: 383(6682), P. 537 - 544

Published: Feb. 1, 2024

Hydrogen atom transfer (HAT) processes can overcome the strong bond dissociation energies (BDEs) of inert C(sp

Language: Английский

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Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 19, 2024

In contemporary drug discovery, enhancing the sp

Language: Английский

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The Carbene Chemistry of N-Sulfonyl Hydrazones: The Past, Present, and Future

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

N-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has tremendous progress chemistry of N-sulfonyl presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Many transfer reactions are unique cannot be achieved by any alternative methods. The discovery novel development highly enantioselective new skeletal editing represent notable recent achievements hydrazones. This review describes overall made hydrazones, organized based on reaction types, spotlighting current state-of-the-art remaining challenges addressed future. Special emphasis is devoted identifying, describing, comparing scope limitations methodologies, key mechanistic scenarios, potential applications complex molecules.

Language: Английский

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