Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation DOI Creative Commons
Jagrit Grover, Gaurav Prakash, Nupur Goswami

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Feb. 28, 2022

Abstract Biaryl scaffolds are found in natural products and drug molecules exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for construction biaryl motifs. However, traditional reactions have limitations like harsh conditions, narrow substrate scope, use additives etc. therefore encouraged synthetic chemists to look alternate greener approaches. This review aims draw general overview on bond formation C–C bonds with aid different methodologies, majorly highlighting sustainable

Language: Английский

Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols DOI

Hiromu Fuse,

Harunobu Mitsunuma, Motomu Kanai

et al.

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(9), P. 4493 - 4499

Published: Feb. 14, 2020

We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising photoredox catalyst, thiophosphate organocatalyst, and nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from α-C-H bond an alcohol substrate thiyl radical photo-oxidized interception generated carbon-centered with β-hydride elimination. in high yield mild conditions without producing side products (except H2 gas) various alcohols, including sterically hindered steroid, pharmaceutical derivative. This also promoted cross-dehydrogenative esterification aldehydes hemiacetal intermediates.

Language: Английский

Citations

143

Automation and computer-assisted planning for chemical synthesis DOI
Yuning Shen, Julia E. Borowski, Melissa A. Hardy

et al.

Nature Reviews Methods Primers, Journal Year: 2021, Volume and Issue: 1(1)

Published: March 18, 2021

Language: Английский

Citations

132

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis DOI

Min‐Jie Zhou,

Lei Zhang, Guixia Liu

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(40), P. 16470 - 16485

Published: Sept. 30, 2021

The value of catalytic dehydrogenation aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting inexpensive organophotoredox base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, process involves H atom transfer (HAT) form alkyl radicals, which then react with cobaloxime produce olefins H2. This operationally simple method enables direct readily available chemical feedstocks diversely functionalized olefins. For example, demonstrate, first time, oxidant-free desaturation thioethers amides alkenyl sulfides enamides, respectively. Moreover, system's exceptional site selectivity functional group tolerance are illustrated late-stage 14 biologically relevant molecules pharmaceutical ingredients. Mechanistic studies have revealed dual HAT provided insights into origin reactivity selectivity.

Language: Английский

Citations

107

Metallaphotoredox catalysis for sp3C–H functionalizations through hydrogen atom transfer (HAT) DOI
Jingchang Zhang, Magnus Rueping

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(12), P. 4099 - 4120

Published: Jan. 1, 2023

sp 3 C–H functionalizations under the combination of photocatalytic HAT and transition metal catalysis.

Language: Английский

Citations

89

Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation DOI Creative Commons
Jagrit Grover, Gaurav Prakash, Nupur Goswami

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Feb. 28, 2022

Abstract Biaryl scaffolds are found in natural products and drug molecules exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for construction biaryl motifs. However, traditional reactions have limitations like harsh conditions, narrow substrate scope, use additives etc. therefore encouraged synthetic chemists to look alternate greener approaches. This review aims draw general overview on bond formation C–C bonds with aid different methodologies, majorly highlighting sustainable

Language: Английский

Citations

82