Environmentally friendly homocoupling reaction of functionalized potassium aryl trifluoroborates salts in aqueous media

Santos-Filho, Everaldo F.; Sousa, Jokderléa C.; Bezerra, Natércia M. M.; Menezes, Paulo H.; Oliveira, Roberta A.

doi:10.1016/j.tetlet.2011.08.008

Cited by 20 publications

(11 citation statements)

References 65 publications

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“…Spectral data were in accordance with those of published results. 14 Mp: 205-207 ° C. 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.38 (d, J = 7.2 Hz, 1H), 7.69 (dd, J = 5.8, 2.5 Hz, 1H), 7.57-7.53 (m, 2H), 7.31–7.24 (m, 3H). 13 C NMR (126 MHz, DMSO- d 6 ) δ 137.0, 133.4, 130.6, 129.0, 129.0, 127.8, 125.7, 125.3, 124.3, 123.8.…”

Section: Discussionmentioning

confidence: 99%

A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid

2015

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A modified Pd-catalyzed method of forming aryl- and heteroarylboron species and a two-step, one-pot borylation/Suzuki-Miyaura cross coupling using the atom economical tetrahydroxydiboron (bis-boronic acid, BBA) is reported. By using ethylene glycol as an additive, the new method results in increased yields, lower BBA loading, faster reaction times, and a broader reaction scope, including previously problematic substrates such as heterocycles.

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Section: Discussionmentioning

confidence: 99%

A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid

2015

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“…In 2011, Menezes and Oliveira et al . reported optimized conditions for the homocoupling of potassium aryl trifluoroborates salts in aqueous media [115] . However, if the aryl groups contain two ortho ‐fluorine substituents, homocoupling products were not observed.…”

Section: Applications Of Fluorinated Aryl Boronates In Organic Synthesismentioning

confidence: 99%

Fluorinated Aryl Boronates as Building Blocks in Organic Synthesis

et al. 2021

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Organoboron compounds are well known building blocks for many organic reactions. However, under basic conditions, polyfluorinated aryl boronic acid derivatives suffer from instability issues that are accelerated in compounds containing an ortho‐fluorine group, which result in the formation of the corresponding protodeboronation products. Therefore, a considerable amount of research has focused on novel methodologies to synthesize these valuable compounds while avoiding the protodeboronation issue. This review summarizes the latest developments in the synthesis of fluorinated aryl boronic acid derivatives and their applications in cross‐coupling reactions and other transformations.

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“…The homocoupling reaction between potassium aryl trifluoroborates containing different functionalities promoted by a catalytic amount of Pd(OAc) 2 was described by Oliveira and co-workers (Scheme 5) [30]. The methodology uses water as a solvent under aerobic conditions to give the corresponding biaryl compounds in good yields.…”

Section: Alternative Solventsmentioning

confidence: 99%