Manganese catalyzed acceptorless dehydrogenative borylation of styrenes DOI Creative Commons
Kuhali Das, Abhishek Kundu, Debashis Adhikari

и другие.

Research Square (Research Square), Год журнала: 2022, Номер unknown

Опубликована: Сен. 19, 2022

Abstract Alkenyl boronate esters are important synthons for various pharmaceuticals, agrochemicals, natural products, and material science. Direct alkene sp2 C-H bond borylation is highly valued its synthesis. However, the drawbacks associated with chemo-, regio- stereoselectivity, using late transition metal catalysts, need sacrificial hydrogen scavengers impeded practicability sustainability. Herein, we utilized a 3d complex as catalyst synthesizing alkenyl via dehydrogenative coupling of styrenes pinacolborane. Hydrogen gas produced sole byproduct without needing an acceptor, making process green atom-economical. The methodology depicted excellent selectivity towards over direct hydroboration. Borylation aromatic alkenes aliphatic ones was also noticed. Derivatives products bioactive molecules underwent successful diversification. product could be employed several drugs potential anticancer agents. Thorough experimental high-level computational studies were performed to delineate reaction pathway. hemilability metal-ligand bifunctionality ligand backbone found crucial catalytic turnover.

Язык: Английский

Synthesis of Borylated Carbocycles by [2 + 2]-Cycloadditions and Photo-Ene Reactions DOI
Jarett M. Posz,

Neetu Sharma,

Paige A. Royalty

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(14), С. 10142 - 10149

Опубликована: Март 27, 2024

Saturated bicyclic compounds make up a valuable class of building blocks in the development agrochemicals and pharmaceuticals. Here, we present synthesis borylated bicyclo[2.1.1]hexanes via crossed [2 + 2]-cycloaddition. Due to presence C–B bond, variety structures can be easily prepared that are not accessible by other methods. Moreover, rare photo-ene reaction is also disclosed, allowing for diastereoselective trisubstituted cyclopentanes.

Язык: Английский

Процитировано

28
The Impact of Boron Hybridisation on Photocatalytic Processes DOI Creative Commons

Alessandro Marotta,

Callum E. Adams,

John J. Molloy

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(38)

Опубликована: Июнь 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.

Язык: Английский

Процитировано

56
Boronic Ester Enabled [2 + 2]-Cycloadditions by Temporary Coordination: Synthesis of Artochamin J and Piperarborenine B DOI
Yanyao Liu, Dongshun Ni, M. Kevin Brown

и другие.

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(41), С. 18790 - 18796

Опубликована: Окт. 6, 2022

A strategy for the photosensitized cycloaddition of alkenylboronates and allylic alcohols by a temporary coordination is presented. The process allows synthesis diverse range cyclobutylboronates. Key to development these reactions alcohol Bpin unit. This not only reaction proceed in an intramolecular manner but also high levels stereo regiocontrol. key aspect studies utility cycloadducts complex natural products artochamin J piperarborenine B.

Язык: Английский

Процитировано

32
Metal–Organic Bichromophore Lowers the Upconversion Excitation Power Threshold and Promotes UV Photoreactions DOI Creative Commons
Han Li, Cui Wang, Felix Glaser

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(20), С. 11402 - 11414

Опубликована: Май 15, 2023

Sensitized triplet–triplet annihilation upconversion is a promising strategy to use visible light for chemical reactions requiring the energy input of UV photons. This avoids unsafe ultraviolet sources and can mitigate photo-damage provide access reactions, which filter effects hamper direct excitation. Here, we report new approach make blue-to-UV more amenable photochemical applications. The tethering naphthalene unit cyclometalated iridium(III) complex yields bichromophore with high triplet (2.68 eV) naphthalene-based reservoir featuring lifetime 72.1 μs, roughly factor 20 longer than photoactive excited state parent complex. In combination three different annihilators, consistently lower thresholds crossover from quadratic into linear excitation power dependence regime were observed compared system composed 2,5-diphenyloxazole annihilator sufficiently robust under long-term blue irradiation continuously high-energy singlet-excited that drive normally light. Both photoredox transfer catalyses feasible using this concept, including reductive N–O bond cleavage Weinreb amides, C–C coupling reaction based on aryl debromination, two Paternò–Büchi [2 + 2] cycloaddition reactions. Our work seems relevant in context developing strategies driving energetically demanding photochemistry low-energy

Язык: Английский

Процитировано

21
Dearomative Construction of 2D/3D Frameworks from Quinolines via Nucleophilic Addition/Borate‐Mediated Photocycloaddition DOI

Asuha Shimose,

Shiho Ishigaki,

Yu Sato

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(41)

Опубликована: Май 28, 2024

Dearomative construction of multiply-fused 2D/3D frameworks, composed aromatic two-dimensional (2D) rings and saturated three-dimensional (3D) rings, from readily available quinolines has greatly contributed to drug discovery. However, dearomative cycloadditions in the presence photocatalysts usually afford 5,6,7,8-tetrahydroquinoline (THQ)-based polycycles, access 1,2,3,4-THQ-based structures remains limited. Herein, we present a chemo-, regio-, diastereo-, enantioselective transformation into 6-6-4-membered without any catalyst, through combination nucleophilic addition borate-mediated [2+2] photocycloaddition. Detailed mechanistic studies revealed that photoexcited borate complex, generated quinoline, organolithium, HB(pin), accelerates cycloaddition suppresses rearomatization occurs conventional Based on our analysis, also developed further photoinduced affording other types frameworks isoquinoline phenanthrene.

Язык: Английский

Процитировано

6
Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis DOI Creative Commons
Yunxiao Zhang, Yizhi Zhang, Chen Ye

и другие.

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Окт. 16, 2022

Abstract Developing photo-induced cascade cyclization of alkene-tethered acylsilanes is challenging, because are unstable under light irradiation. Herein, we report that the energy transfer from excited to a photocatalyst possesses lower triplet can inhibit undesired decomposition acylsilanes. With neutral Eosin Y as photocatalyst, an efficient synthesis cyclopentanol derivatives achieved with and allylic sulfones. The reaction shows broad substrate scope synthetic potential this transformation highlighted by construction which contain fused-ring or bridged-ring.

Язык: Английский

Процитировано

26
Electrochemical assembly of isoxazoles via a four-component domino reaction DOI Creative Commons
Yuanyuan Zhao, Xinyue Li, Simon L. Homölle

и другие.

Chemical Science, Год журнала: 2023, Номер 15(3), С. 1117 - 1122

Опубликована: Дек. 11, 2023

Multicomponent domino reactions

Язык: Английский

Процитировано

14
The current utility and future potential of multiborylated alkanes DOI

Kane A. C. Bastick,

Dean D Roberts,

Allan J. B. Watson

и другие.

Nature Reviews Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 26, 2024

Язык: Английский

Процитировано

5
Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of ChiralC2‐Symmetric Bis(phosphine) Ligands DOI
Ming Cui, Zhiyuan Zhao, Martin Oestreich

и другие.

Chemistry - A European Journal, Год журнала: 2022, Номер 28(62)

Опубликована: Июль 11, 2022

Chiral bis(phosphine) monooxides (BPMOs) derived from C

Язык: Английский

Процитировано

20
Photosensitized [2 + 2]-Cycloadditions of Dioxaborole: Reactivity Enabled by Boron Ring Constraint Strategy DOI
Yanyao Liu, M. Kevin Brown

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(46), С. 25061 - 25067

Опубликована: Ноя. 8, 2023

A strategy to achieve photosensitized [2 + 2] cycloadditions by means of temporary ring constraint is reported. Specifically, a dioxaborole prepared that undergoes with wide variety alkenes. This overcomes some challenges the cycloaddition acyclic substrates. The products can be easily transformed into cyclobutyl diols or 1,4-dicarbonyl compounds; latter represents formal alkene vicinal diacylation. synthetic utility this method shown in synthesis valuable heterocycles and biatriosporin D.

Язык: Английский

Процитировано

11