Biological and Medicinal Applications of Boronic Acids

Yang, Wenqian; Gao, Xingming; Wang, Binghe

doi:10.1002/3527606548.ch13

Cited by 47 publications

(34 citation statements)

References 100 publications

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“…11 There have also been extensive studies on biological and medicinal applications of boronic acids for 10 B carriers of neutron capture therapy and proteasome inhibitor for cancer therapy. Such chemistry of boronic acids is summarized in this review, 12 but this review is mainly restricted to our own efforts in metal-catalyzed reactions.…”

Section: Introductionmentioning

confidence: 99%

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Miyaura¹

2008

Bulletin of the Chemical Society of Japan

367

110

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Metal-catalyzed B-C and C-C bond-forming reactions of organoboronic acids that have been pursued in the past three decades by our group are summarized in this article. B-C bond-forming reactions for the synthesis of organoboronic acid derivatives include metal-catalyzed addition reactions of pinacolborane or catecholborane (hydroboration), bis(pinacolato)diboron (diboration), and alkylthioboranes (thioboration) to alkenes, alkynes, 1,3-alkadienes, or 1,2-alkadienes (allenes). Other B-C bond-forming reactions include coupling reactions of pinacolborane or bis(pinacolato)diboron for borylation of C-halogen bonds with palladium catalysts and C-H bonds of arenes and alkenes with iridium catalysts. These reactions have provided a convenient new access to aryl-, 1-alkenyl-, allyl-, or benzylboronates. Metal-catalyzed C-C and C-N bond-forming reactions using boronic acid derivatives include synthesis of novel cyclic triolborate salts for palladium-or copper-catalyzed cross-coupling reactions with organic halides or amines, rhodium-or palladiumcatalyzed 1,4-addition reactions of arylboronic acids to ,-unsaturated carbonyl compounds and rhodium-catalyzed addition of aryl-and 1-alkenylboronic acids to aldehydes and imines.

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Section: Introductionmentioning

confidence: 99%

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Miyaura¹

2008

Bulletin of the Chemical Society of Japan

367

110

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“…In some studies, the catechol moiety of DOPA form strong, reversible interactions with metal ions, leading to the formation of rapid self-healing smart materials [15][16][17]. Boric acid is a typical Lewis acid, which can react with water to abstract OH − in aqueous media and convert the trigonal boron to an anionic tetrahedral geometry [18]. Under alkaline conditions, the boron atom has four coordinative bonds to form bis-complexes with diols from catechol groups.…”

Section: Introductionmentioning

confidence: 99%

Self-healable mussel-mimetic nanocomposite hydrogel based on catechol-containing polyaspartamide and graphene oxide

Wang

Jeon

Park

et al. 2016

Materials Science and Engineering: C

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“…Boronic acids are known to form tight complexes with cis-1,2-diols, and their use as carbohydrates or nucleosides sensors has lately attracted much attention. [26][27][28] The development of new fluorescent sensors with high specificity is therefore of particular interest. Recently, Zheng et al aimed at obtaining of such triazole-based sensors by reporting a two-step sequence for the synthesis of ethynyl boronates that could be used in the 1,3-dipolar cycloaddition, 21 but to our knowledge, no fluorescent sensor of this type has been reported in the literature.…”

mentioning

confidence: 99%

Sequential Seyferth-Gilbert/CuAAC Reactions: Application to the One-Pot Synthesis of Triazoles from Aldehydes

Luvino¹,

Amalric²,

Smietana³

et al. 2007

Synlett

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A reliable and operationally simple one-pot reaction for a one-carbon homologation of various aldehydes followed by a Cucatalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) is reported. 1,4-Disubstituted 1,2,3-triazoles are obtained in good to excellent yields from a variety of readily available aldehydes without the need for isolation of the alkyne intermediates. The reaction has a broad scope, allows the formation of new bioconjugates and is applied for the synthesis of new boronic acid based fluorescent sensors.

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Biological and Medicinal Applications of Boronic Acids

Cited by 47 publications

References 100 publications

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Self-healable mussel-mimetic nanocomposite hydrogel based on catechol-containing polyaspartamide and graphene oxide

Sequential Seyferth-Gilbert/CuAAC Reactions: Application to the One-Pot Synthesis of Triazoles from Aldehydes

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