Photoinduced aerobic C–S borylation of aryl sulfides

Li, Xin-Qi; Wan, Zhinian; Hu, Xiaoyun; Zhang, Hua

doi:10.1039/d2qo00240j

Cited by 8 publications

(4 citation statements)

References 52 publications

(56 reference statements)

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“…[51] By employing this strategy, remarkable para-selective CÀ H borylation of monosubstituted benzenes was realized, which might attribute to the incredible electrophilicity of thianthrene dication intermedi- The visible-light photoinduced metal-free CÀ S borylation of less activated aryl sulfides with B 2 pin 2 was realized by our group employing simple and mild conditions (Scheme 27). [52] Under blue LED irradiation, aryl sulfides with various functional groups were converted to aryl boronate esters under ambient conditions using 1,4-benzoquinone as the photosensitizer. A radical borylation mechanism involving O 2 *À was proposed.…”

Section: Aromatic Cà S Borylationmentioning

confidence: 99%

“…The visible‐light photoinduced metal‐free C−S borylation of less activated aryl sulfides with B 2 pin 2 was realized by our group employing simple and mild conditions (Scheme 27). [52] Under blue LED irradiation, aryl sulfides with various functional groups were converted to aryl boronate esters under ambient conditions using 1,4‐benzoquinone as the photosensitizer. A radical borylation mechanism involving O 2 ⋅ − was proposed.…”

Section: Aromatic C−s Borylationmentioning

confidence: 99%

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Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Luo

Tang

et al. 2023

The Chemical Record

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Aromatic organoboron compounds are highly valuable building blocks in organic chemistry. They were mainly synthesized through aromatic C−H and C−Het borylation, in which transition metal‐catalysis dominate. In the past decade, with increasing attention to sustainable chemistry, numerous transition metal‐free C−H and C−Het borylation transformations have been developed and emerged as efficient methods towards the synthesis of aromatic organoboron compounds. This account mainly focuses on recent advances in transition metal‐free aromatic C−H, C−N, C−S, and C−O borylation transformations and provides insights to where further developments are required.

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Section: Aromatic Cà S Borylationmentioning

confidence: 99%

Section: Aromatic C−s Borylationmentioning

confidence: 99%

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Luo

Tang

et al. 2023

The Chemical Record

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“…他们通过改变反应条件中的催化剂和碱, 在相似的体系下实现了二芳基硫醚和二芳基 (亚)砜的碳-硫键硼化反应. 2022 年, 我们课题组 [45] 报道了无过渡金属参与的可见光诱导下芳基硫化物的直接碳-硫键硼化反应(Scheme 15, d). 该方案以蓝色 LED 作为光源, 1,4-苯醌作为光敏剂, 在空气室温的条件下就能将各种官能团取代的芳基硫化物转化为芳基硼酸酯.…”

Section: 芳基肼盐酸盐的光化学硼化反应unclassified

Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds

Du¹,

Zhang²

2023

Chinese Journal of Organic Chemistry

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Organoboron compounds are important building blocks in organic synthesis and have been widely applied in materials and pharmaceutical science. The development of practical and concise borylation reactions to synthesize organoboron compounds has always been one of the core topics of organoboron chemistry. Recently, photochemical and electrochemical borylation reactions have gained rapid development and emerged as important methods towards the synthesis of organoboron compounds. The recent research progress concerning photochemical, electrochemical and photoelectrochemical borylation involving aryl and alkyl compounds from the view of energy resources and substrates is reviewed. Additionally, research trends of this area are also discussed.

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“…Despite their synthetic versatility, the preparation of these compounds can be challenging, and these compounds can be unstable, with limited structure, or their synthesis may require forcing reaction conditions that somewhat limit their application. Among them, mild phenyl/aryl radical reactions are more suitable for the development of borylation 20 – 26 .…”

Section: Introductionmentioning

confidence: 99%

Photocatalytic direct borylation of carboxylic acids

et al. 2022

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The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.

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Photoinduced aerobic C–S borylation of aryl sulfides

Abstract: The direct C–S borylation of aryl sulfides with B2pin2 has been achieved via a transition-metal-free photochemical process. With blue LED irradiation, aryl sulfides with various functional groups were converted to...

Cited by 8 publications

References 52 publications

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds

Photocatalytic direct borylation of carboxylic acids

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