Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes

Chen, Yu; Au, Yik Ki; Quan, Yangjian; Xie, Zuowei

doi:10.1007/s11426-018-9388-3

Cited by 56 publications

(26 citation statements)

References 78 publications

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“…The side reactions were also suppressed to a great extent. Very recently, with the assistance of a bidentate directing group (8‐aminoquinoline), B(4)−H alkynylation of carboranyl amides with aromatic terminal alkynes was also achieved, mediated by a copper complex . Unlike catalytic systems aforementioned without external oxidants (dihydrogen was released directly), this reaction required over stoichiometric Cu(OTf) 2 (2 equiv) and Ag 2 CO 3 (2 equiv).…”

Section: Formation Of Spc−heteroatom Bondsmentioning

confidence: 99%

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

et al. 2020

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Section: Formation Of Spc−heteroatom Bondsmentioning

confidence: 99%

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

et al. 2020

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“…Разработан прямой и эффективный метод синтеза ранее неизвестных C,B-замещенных конденсированных карборанилпиридонов 60 с помощью реакции [4+2]циклоприсоединения о-карбораниламидов с алкинами, катализируемой трифторметансульфонатом меди (II) (схема 24) [59].…”

Section: -49unclassified

Chemical modification of different compounds with nitrogen-containing heterocycles

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Дикусар

2021

Vescì Akademìì navuk Belarusì. Seryâ himičnyh navuk

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Heterocyclic compounds have an extremely important practical application, since many heterocycles are the basis of the most valuable medicinal substances, both natural (vitamins, enzymes, alkaloids, etc.) and synthetic biologically active compounds. The work mainly considers the most relevant directions for various purposes drugs search by modifying known bioactive natural, organoelement and framework compounds with 1,2-azole, oxazole, oxadiazole, thiazole, triazole, pyridine, pyrimidine heterocycles over the past 10 years. Chemical modification makes it possible to increase the water solubility of the compounds, which is important when choosing the pathways for the most rational drug introduction into the body, to reduce the toxicity of the corresponding substances, to increase the breadth of the therapeutic action, and also to give new valuable medicinal properties, thus significantly expanding their application in medicine and agriculture.

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“…Cage boron-alkynylated carboranes can be synthesized through a Pd-catalyzed cross-coupling reaction of boron-iodinated carboranes with alkynyl Grignard reagents . Recently, our group demonstrated the synthesis of B(4)-alkynylated o -carboranes by either Pd-catalyzed or Cu-mediated B–H/C–H cross dehydrocoupling (Scheme a) . For the synthesis of cage carbon-alkynylated o -carboranes, there are only two methods reported so far.…”

Section: Introductionmentioning

confidence: 99%

Transition-Metal-Free Cross-Coupling Reaction of Iodocarboranes with Terminal Alkynes Enabled by UV Light: Synthesis of 1-Alkynyl-o-Carboranes and Carborane-Fused Cyclics

Xie

2020

J. Am. Chem. Soc.

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A transition-metal-free coupling protocol between iodocarboranes and terminal alkynes enabled by light at room temperature has been developed, leading to the synthesis of a variety of 1-alkynyl-o-carboranes. Moreover, following this strategy, the introduction of 1-I-3-aryl-o-carboranes or 1-I-2-aryl-o-carboranes results in the formation of o-carborane-fused cyclics. Interestingly, when 1-I-3-(p-R-C6H4)-o-carboranes are chosen as coupling partners, unexpected R-group migration products are also isolated. On the basis of the results of control experiments and isolation of the key intermediates, a possible reaction mechanism is then proposed, involving the formation of spiro radical species.

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Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes

Cited by 56 publications

References 78 publications

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

Chemical modification of different compounds with nitrogen-containing heterocycles

Transition-Metal-Free Cross-Coupling Reaction of Iodocarboranes with Terminal Alkynes Enabled by UV Light: Synthesis of 1-Alkynyl-o-Carboranes and Carborane-Fused Cyclics

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