Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)–tricyclohexylphosphine complexes

Ishiyama, Tatsuo; Ishida, Kousaku; Miyaura, Norio

doi:10.1016/s0040-4020(01)00998-x

Cited by 299 publications

(156 citation statements)

References 42 publications

(4 reference statements)

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“…In fact, this kind of transformation had already been performed by other groups on various triflate substrates. [46] Among these, T. Ishiyama's conditions [46b] appeared especially appealing to us because of their usually very high yields. Fortunately, this was also the case when we applied these conditions to the palladium-catalyzed borylation of 8 with bis(pinacolato)diboron, which provided the desired diboronic acid ester 18 [47] in almost quantitative yield (Scheme 7).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes

et al. 2005

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Racemic dissymmetric 2,2'‐dihydroxy‐9,9'‐spirobifluorene was prepared and resolved by clathrate formation with (R,R)‐(+)‐2,3‐dimethoxy‐N,N,N',N'‐tetracyclohexylsuccindiamide, giving rise to both enantiomers in very good yields. The absolute stereochemistry of the resolved material could be assigned by an X‐ray structure analysis of single crystals of the clathrate. Enantiomerically pure diols could be transformed into the corresponding ditriflates, which were then used as starting materials in different cross‐coupling procedures to provide a number of new enantiomerically pure spiro compounds bearing versatile functional groups suitable for further elaboration, as demonstrated by some examples. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes

et al. 2005

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“…The less reactive chloroarenes are also efficient precursors to boronic acid derivatives in the presence of Pd(dba) 2 and PCy 3 (Scheme 3). 17 The catalyst can also be effective for carrying out the coupling reaction of the less reactive aryl bromide or triflates bearing electrondonating substituents under mild conditions.…”

Section: Preparation Of Boronic Acids and Their Derivativesmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

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“…Borylation of aryl, 1-alkenyl, allyl, and benzyl halides 18,46 or triflates 47 proceeds in the presence of KOAc and a palladium catalyst (Scheme 7). PdCl 2 (dppf) has been used for representative aromatic iodides and bromides 48 and 49, 18 and a combination of a palladium precursor and an electron-donating PCy 3 46 46 or N-heterocyclic carbene (NHC, 47) 48 can be advantageous for achieving high yields for aryl chlorides and electron-rich aryl bromides or triflates.…”

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confidence: 99%

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Miyaura¹

2008

Bulletin of the Chemical Society of Japan

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365

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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Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)–tricyclohexylphosphine complexes

Cited by 299 publications

References 42 publications

Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes

Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

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