Cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides

Molander, Gary A.; Yun, Chang‐Soo

doi:10.1016/s0040-4020(02)00009-1

Cited by 72 publications

(49 citation statements)

References 31 publications

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“…Traditionally, Suzuki cross-coupling reactions with alkyl boronic acids were thought to be non-viable, due to their low nucleophilicity and tendency for b-hydride elimination after transmetallation. 32 Over recent years this has been proved to be wrong with pioneering work by Falck, 33 Molander 34 and Fu, 35 who have shown that, by judicious choice of catalyst and conditions, clean Suzuki crosscoupling of alkyl-boronic acids is possible.…”

Section: Preparation and Application Of Functionalised Organoboron Rementioning

confidence: 99%

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

et al. 2005

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Section: Preparation and Application Of Functionalised Organoboron Rementioning

confidence: 99%

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

et al. 2005

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“…Initially, Suzuki coupling using the commercially available PdCl 2 (dppf)· CH 2 Cl 2 complex (15) was tried, but it was not effective and resulted in decomposition of 13 ( Table 1, Entry 1). [17] Upon changing to a weaker base (K 2 CO 3 ), the reaction proceeded but was incomplete even after 60 h of refluxing in THF ( [18] We then examined the reaction at higher temperatures in other solvents. While the use of DMF resulted in the decomposition of 13, the Suzuki cou-pling was complete at a comparable temperature in refluxing DME to give an 81 % yield of 12a (Table 1, Entry 5).…”

Section: Resultsmentioning

confidence: 99%

A Protecting‐Group‐Free Route to Chiral BINOL–Phosphoric Acids

Chiu

2011

Eur J Org Chem

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A two‐step, protecting group‐free route for the synthesis of 3,3′‐disubstituted and 6,6′‐disubstituted chiral BINOL–phosphoric acids has been realized starting from commercially available brominated BINOLs. This synthesis relies on the direct Suzuki coupling of brominated BINOL phosphoric acids. This synthetic strategy is more efficient compared to previous circuitous strategies involving protections and deprotections, and the process is higher yielding relative to the alternative two‐step synthesis involving Suzuki coupling of the BINOL.

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“…Using the same catalyst but a less expensive procedure, Molander and co-workers were able to couple 2-phenylethylboronic acid with either electron-deficient or electron-excessive aryl bromides. [16] Sterically congested 2-bromotoluene or 1-bromonaphthalene were also employed successfully. These couplings were achieved by use of PdCl 2 (dppf) (9 mol-%) in the presence of K 2 CO 3 in a mixture of THF and H 2 O (Scheme 6).…”

Section: Methodsmentioning

confidence: 99%

“…[79,80] With PdCl 2 (dppf) as catalyst and Cs 2 CO 3 or K 2 CO 3 as bases, a variety of aryl triflates were coupled with methylboronic acid or 2-phenylboronic acid (Scheme 57). [16] The yields of the reactions with various aryl triflates were high Scheme 56. regardless of the position of the functional group on the ring, and even the nitro group was tolerated. It should be noted that in general B-alkyl-9-BBN coupling reactions provide mixtures of reduced anilines with such substrates.…”

Section: Alkylations Of Aryl or Alkenyl Triflates With Alkylboronic Amentioning

confidence: 99%

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

2008

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Palladium‐catalysed Suzuki–Miyaura cross‐couplings of organoboronic acids or organotrifluoroborates with aryl and alkenyl halides or triflates have become classic methods for generating carbon–carbon bonds. For this reaction, not only sp2‐hybridized but also sp3‐hybridized organoboron derivatives can be employed. However, alkylboronic acids or trifluoroborates are generally less reactive than arylboron derivatives. The coupling of primary alkylboronic acids or alkyltrifluoroborates with aryl or alkenyl halides is well known, and the reaction gives the coupling products with high selectivities, relatively high turnover numbers and in good yields with several catalysts. On the other hand, secondary alkylboronic acids or trifluoroborates, except for cyclopropylboron derivatives, are much less reactive, and very few catalyst are able to activate such compounds. Because of the hybridization of cyclopropanes, which confers significant aromatic character, several reactions have successfully been performed with cyclopropylboronic acids or trifluoroborates. The stereochemistries of substituted cyclopropylboron derivatives were maintained in the course of the reactions. For all these couplings with primary or secondary alkylboron derivatives, aryl iodides, bromides, chlorides or triflates and alkenyl iodides, bromides or triflates were employed. Alkenyl chlorides have attracted less attention. The reactions with alkenyl halides are stereoselective. A few examples of couplings between sp3‐hybridized organoboronic acids and alkyl halides have also been reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides

Cited by 72 publications

References 31 publications

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

A Protecting‐Group‐Free Route to Chiral BINOL–Phosphoric Acids

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

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