Potassium Trifluoro(organo)borates: New Perspectives in Organic Chemistry

Darses, Sylvain; Genêt, Jean‐Pierre

doi:10.1002/ejoc.200300294

Cited by 335 publications

(124 citation statements)

References 90 publications

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“…[3][4][5] Many of these molecules have increasingly been used in a variety of newly discovered chemical processes, and as key functional components in other areas, including molecular receptors, molecular sensors, novel materials, as well as biological probes and pharmaceuticals. …”

Section: Long History -Expanding Rolesmentioning

confidence: 99%

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Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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The present essay offers an overview of the latest developments in the chemistry of organoboron compounds. The unique structural characteristics and the versatile reactivity profile of organoboron compounds continue to expand their roles in several areas of chemistry. A growing number of boron-mediated reactions have become vital tools for synthetic chemistry, particularly in asymmetric synthesis, metal-catalyzed processes, acid catalysis, and multicomponent reactions. As a result, boronic acids and related molecules have now evolved as major players in synthetic and medicinal chemistry. Moreover, their remnant electrophilic reactivity, even under physiological conditions, has allowed their incorporation in a growing number of bioactive molecules, including bortezomib, a clinically approved anticancer agent. Finally, the sensitive and selective binding of boronic acids to diols and carbohydrates has led to the development of a growing number of novel chemosensors for the detection, quantification, and imaging of glucose and other carbohydrates. There is no doubt that the chemistry of organoboron compounds will continue to expand into new discoveries and new applications in several fields of science. Long History -Expanding RolesOrganic compounds containing boron have been known for over a century, and many aspects of their chemical properties and reactivity have been known for quite some time. Since the discovery and development of hydroboration, the resulting organoboranes are among the most widely used reagents and intermediates in organic synthesis including asymmetric reactions. Also, early investigations on the chemistry of boron hydrides and carboranes revealed new classes of compounds with unique structure and reactivity that continue to attract attention. Despite these early discoveries, however, the real potential of some of the more versatile and chemically stable organoboron compounds was not realized until recently.Indeed, the growing list of valuable organoboron compounds in addition to organoboranes [1] now includes organoboronic acids and boronates, [2] and more recently organotrifluoroborates.

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Section: Long History -Expanding Rolesmentioning

confidence: 99%

“…Highly electrophilic boron compounds, such as BF 3 and related molecules, are well known Lewis acids that can mediate several chemical transformations. However, these molecules require anhydrous conditions because they react readily with water.…”

Section: Acid Catalysismentioning

confidence: 99%

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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“…Sodium benzenesulfinate produced the corresponding 2-phenylpyridine in 80% yield (Table 4, entry 11). It was noted that the 2-furyl, 3-pyridinyl and 4-indolyl sodium heteroaryl trifluoroborate were successfully reacted with 2-pyridinylsulfinate to afford heteroaryl-2-pyridine derivatives in 57%-73% yields (Table 4, entries [12][13][14].…”

Section: Resultsmentioning

confidence: 99%

“…Trifluoroborates are increasingly important reagents because of their favorable physical and chemical properties; additionally, they offer an alternative to toxic organometallic species such as organostannanes. [8][9][10][11][12][13][14][15] The tetracoordinate nature of the trifluoroborates makes them resistant to a variety of reaction conditions. This characteristic allows one to build complexity into a molecule while leaving the carbon−boron bond intact.…”

Section: Introductionmentioning

confidence: 99%

Pd‐catalyzed Desulfitative reaction of Aryltrifluoroborates with sodium Arenesulfinates in water

Sheng

Sun²,

Zhang

et al. 2017

Applied Organom Chemis

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An efficient procedure for the synthesis of biaryls was catalyzed by Pd(CH 3 CN) 4 (BF 4 ) 2 is reported. This Pd-catalyzed cross-coupling reaction of aryltrifluoroborates with sodium arenesulfinates was developed under mild and environmentally benign conditions, in water without any ligand or additive. The reaction gave a range of structurally diverse unsymmetrical bi-aryl molecules with excellent yields, in which the byproduct was sulfur dioxide. It is worth noting that this protocol is also applicable to many heterocyclic aromatics such as thiophene, furan, pyridine, quinoline, isoquinoline and indole.

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“…38 Since then, many have reported on their utility and advantages such as: atom economy compared to boronic acids and esters, their ease of purification and disposal, their monomeric rather than trimeric nature, and their air stability. 39,40 Given…”

Section: Resultsmentioning

confidence: 99%

Preparation of 1,3-dienyl organotrifluoroborates and their Diels–Alder/cross-coupling reactions

Day

Welker

2007

Tetrahedron

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Potassium Trifluoro(organo)borates: New Perspectives in Organic Chemistry

Cited by 335 publications

References 90 publications

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Pd‐catalyzed Desulfitative reaction of Aryltrifluoroborates with sodium Arenesulfinates in water

Preparation of 1,3-dienyl organotrifluoroborates and their Diels–Alder/cross-coupling reactions

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