The Impact of Boron Hybridisation on Photocatalytic Processes

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(38)

Published: June 24, 2022

Recently the fruitful merger of organoboron chemistry and photocatalysis has come to forefront organic synthesis, resulting in development new technologies access complex (non)borylated frameworks. Central success this combination is control boron hybridisation. Contingent on photoactivation mode, as its neutral planar form or tetrahedral boronate can be used regulate reactivity. This Minireview highlights current state art photocatalytic processes utilising compounds, paying particular attention role hybridisation for target transformation.

Language: Английский

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Alkyl Radical Generation from Alkylboronic Pinacol Esters through Substitution with Aminyl Radicals

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(16), P. 8770 - 8775

Published: April 14, 2023

Alkylboronic pinacol esters (APEs) are highly versatile reagents in organic synthesis. However, the direct generation of alkyl radicals from commonly used, bench-stable APEs has not been well explored. In this communication, radical through reaction with aminyl is reported. The readily generated by visible-light-induced homolytic cleavage N-N bond N-nitrosamines, and C occurs nucleohomolytic substitution at boron. As an application, efficient photochemical alkyloximation alkenes N-nitrosamines under mild conditions presented. A wide range primary, secondary, tertiary engage transformation that easily scaled up.

Language: Английский

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Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Sept. 14, 2023

In recent years, numerous 1,2-R shift (R = aliphatic or aryl) based on tetracoordinate boron species have been well investigated. the contrary, corresponding radical migrations, especially 1,2-boryl for construction of organoborons is still in its infancy. Given paucity and significance such strategies chemistry, it urgent to develop other efficient alternative synthetic protocols enrich these underdeveloped 1,2-boron before their fundamental potential applications could be fully explored at will. Herein, we demonstrated a visible-light-induced photoredox neutral decarboxylative cross-coupling reaction, which undergoes give translocated C-radical further capture versatile acceptors. The mild reaction conditions, good functional-group tolerance, broad β-boryl NHPI esters scope as acceptors make this protocol applicable modification bioactive molecules. It can expected that methodology will very useful tool an strategy primary via novel mode.

Language: Английский

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Tunable vicinal, geminal diphosphorylation and C–N bond phosphorylation of enaminones toward divergent phosphorylated ketone derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6383 - 6386

Published: Jan. 1, 2023

The tunable reactions of enaminones with phosphine oxides/phosphonates in the form vicinal- and geminal diphosphorylation, C–N bond phosphorylation have been developed, providing new methods for synthesis divergent phosphorylated molecules.

Language: Английский

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The current utility and future potential of multiborylated alkanes

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 26, 2024

Language: Английский

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Transition-metal-free C(sp2)–C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(12), P. 1211 - 1221

Published: Aug. 3, 2023

Language: Английский

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Hetero-Single-Atom F and P-Doped Layered Graphitic Carbon Nitride Nanosheets for Electrochemical Quantification of Vanillin in Food Samples

ACS Applied Nano Materials, Journal Year: 2024, Volume and Issue: 7(7), P. 7248 - 7257

Published: March 20, 2024

In this article, we present the preparation of a novel heteroatom halogen (fluorine) and nonmetal phosphorus-doped layered graphitic carbon nitride, via thermal decomposition technique, examined its electrochemical monitoring ability for vanillin detection. The materials' basic properties have been observed with various analytical analyses such as X-ray diffractometry, field-emission scanning electron microscopy, photoelectron spectroscopy, transmission microscopy. proposed sensor material was under operating conditions to demonstrate good current response sensing. has wide linear range (0.2–100 μM) lower limit detection (LoD = 15 nM) an enhanced sensitivity 1.80 μA μM–1 cm–2. Ultimately, potential utility suggested effectively tested on food samples, demonstrating exceptional recoveries 99.46 96.76% coffee vanilla ice cream, respectively, corresponding relative standard deviations 1.83 1.21 each.

Language: Английский

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Catalytic Selective Functionalization of Poly(organoborons)^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 28, 2024

Comprehensive Summary Organoborons are commonly used building blocks for rapidly increasing molecular complexity. Although significant progress has been made in the selective functionalization of mono‐organoborons, site‐selective poly(organoborons) attracted substantial interest organic synthesis, pharmaceuticals, and agrochemicals due to presence multiple potential reaction sites. This review discusses various activation modes target C–B bond, with diverse transformations being achieved both a efficient manner. Recent advances catalytic 1, n ‐diboronates through ionic radical pathways highlighted. Furthermore, we summarize existing challenges future research directions this field. Key Scientists In 1993, Suzuki, Miyaura coworkers developed pioneering example arylation towards cis‐1,2‐bis(boryl) alkenes, marking inception The Morken group contributions asymmetric diboration alkenes realized elegant these compounds since 2004. 2016, Fernández colleagues internal bond tri(boronates). Since 2019, Aggarwal Giese‐type addition at more substituted 1,2‐bis(boronic) esters photoredox catalysis. controllable regiodivergent alkynylation 1,3‐bis(boronic) was by Gao 2023. Recently, Qin conducted on programmable late‐stage bridge‐substituted bicyclo[1.1.1]pentane (BCP) bis‐boronates. 2013, stereoselective have several groups, including those led Chen. summarizes latest most developments field 1993.

Language: Английский

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Photoinduced Assembly of Diverse Homoallylic Boronates from gem-Diborons

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

In comparison to alkyl monoboron or 1,2-diboron, which can generate radicals via tetracoordinate boron species under photocatalytic conditions, the participation of gem-diborons as substrates in such reactions remains be developed. Herein, we report a method utilizing starting materials α-boryl radicals, then react with various olefins, successfully and efficiently constructing diverse range high-value homoallylic boronates; meanwhile, gem-difluorohomoallylic skeletons could also smoothly obtained. This transformation demonstrates broad substrate scope excellent tolerance toward functional groups, enhancing utility gem-diboron precursors for C-C bond construction production valuable products.

Language: Английский

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Synthesis of α-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2928 - 2933

Published: April 18, 2023

α-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional methods α-haloboronates are harsh and complicated. Herein, we used nBuLi the nucleophilic reagent to attack boron atom gem-diborylalkanes form tetracoordinate species successfully achieved α-chloroboronates α-bromoboronates with readily accessible electrophilic halogen reagents (NCS NBS). The reaction is transition-metal-free features broad substrate scope diversified valuable products.

Language: Английский

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