Green Chemistry, Journal Year: 2024, Volume and Issue: 26(12), P. 7357 - 7362
Published: Jan. 1, 2024
Herein, we report an operationally simple addition of hydrazones to carbonyl compounds using earth-abundant metal, under aqueous and aerobic conditions.
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(40), P. 21624 - 21634
Published: May 15, 2021
Abstract Carbonyl Umpolung is a powerful strategy in organic chemistry to construct complex molecules. Over the last few years, versatile catalytic approaches for generation of acyl anion equivalents from carbonyl compounds have been developed, but methods obtain alkyl carbanions fashion are still at an early stage. This Minireview summarizes recent progress through Umpolung. Two different can be utilized enable compounds: Wolff–Kishner reaction and single‐electron reduction imines. We discuss scope, mechanistic insights, synthetic applications as well potential future developments.
Language: Английский
Citations
76
Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(10)
Published: Nov. 15, 2021
The simple and efficient conversion of carbonyl compounds into functionalized alkanes via deoxygenation is highly enabling in chemical synthesis. This Review covers the recent methodology development carboxyl deoxygenative functionalizations, highlighting some representative significant contributions this field. These advances are categorized based on reactivity patterns oxygenated feedstock compounds, including aldehydes, ketones carboxylic acids. Four types reactive intermediates arising from aldehydes during deoxygenation, namely, bis-electrophiles, carbenoids, bis-nucleophiles alkyl radical equivalents, presented, while acids mainly behave as tris-electrophiles when deoxygenated. In each subcategory, selected examples organized according to type bond formation discussed a generalized mechanistic perspective.
Language: Английский
Citations
62
Organic Letters, Journal Year: 2020, Volume and Issue: 22(5), P. 1742 - 1747
Published: Feb. 13, 2020
The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH3 has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use the advantage photoredox catalysis to generate key boryl radical direct activation B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing wide array valuable polyfluoroarylboron compounds. Moreover, both computational experimental studies were performed illustrate reaction mechanism.
Language: Английский
Citations
54
The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 3394 - 3410
Published: April 14, 2021
Abstract The activation of a carbon‐fluorine bond is one the most challenging topics in modern synthetic organic chemistry due to their low reactivity compared other carbon‐halogen bonds. In this review, we present recent developments since 2015 on cross‐coupling reactions that form C−C bonds via cleavage C( sp 2 )−F Not only conventional bonds, but also decarbonylative or carbonyl‐retentive C(acyl)−F will be introduced. This paper mainly describes new protocols for formation )−C( 3 ), and ) transition‐metal‐catalyzed
Language: Английский
Citations
48
Chemical Science, Journal Year: 2021, Volume and Issue: 12(47), P. 15511 - 15518
Published: Jan. 1, 2021
Modulating the reaction selectivity is highly attractive and pivotal to rational design of synthetic regimes. The defluorinative functionalization
Language: Английский
Citations
46
Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)
Published: June 17, 2021
Aldehydes and ketones are widely found in biomass resources play important roles organic synthesis. However, the direct deoxygenative coupling of aldehydes or to construct C(sp3)-C(sp3) bond remains a scientific challenge. Here we report nickel-catalyzed reductive homo-coupling moisture- air-stable hydrazones generated in-situ from naturally abundant challenging bond. This transformation has great functional group compatibility can suit broad substrate scope with innocuous H2O, N2 H2 as by-products. Furthermore, application several biological molecules PEEK model demonstrate generality, practicability, applicability this novel methodology.
Language: Английский
Citations
33
Chemical Science, Journal Year: 2022, Volume and Issue: 13(24), P. 7165 - 7171
Published: Jan. 1, 2022
A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, were used as alternatives to organometallic reagents, in the absence a transition metal or an external photosensitizer, making mild green. The protocol compatible variety functionalities, including methyl, methoxy, trifluoromethyl, halogen, heteroaromatic rings. Mechanistic investigations showed that association hydrazone anion halides formed electron donor-acceptor complex, which when excited visible light generated radical via single-electron transfer.
Language: Английский
Citations
27
Pure and Applied Chemistry, Journal Year: 2023, Volume and Issue: 95(5), P. 465 - 474
Published: Jan. 10, 2023
The modern synthetic chemistry heavily relies on the use of stoichiometric organometallic reagents to react with various electrophiles. dependence quantities metals and often organic halides as precursors, in turn both produces copious amounts metal halide wastes well leads concerns future sustainability. Inspired by classical Wolff-Kishner reduction, our lab has recently developed a general strategy
Language: Английский
Citations
11
Angewandte Chemie, Journal Year: 2021, Volume and Issue: 134(10)
Published: Nov. 15, 2021
Abstract The simple and efficient conversion of carbonyl compounds into functionalized alkanes via deoxygenation is highly enabling in chemical synthesis. This Review covers the recent methodology development carboxyl deoxygenative functionalizations, highlighting some representative significant contributions this field. These advances are categorized based on reactivity patterns oxygenated feedstock compounds, including aldehydes, ketones carboxylic acids. Four types reactive intermediates arising from aldehydes during deoxygenation, namely, bis‐electrophiles, carbenoids, bis‐nucleophiles alkyl radical equivalents, presented, while acids mainly behave as tris‐electrophiles when deoxygenated. In each subcategory, selected examples organized according to type bond formation discussed a generalized mechanistic perspective.
Language: Английский
Citations
23
Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 9
Published: Feb. 12, 2025
Language: Английский
Citations
0