Recent advances in organotrifluoroborates chemistry

Stefani, Hélio A.; Cella, Rodrigo; Vieira, Adriano S.

doi:10.1016/j.tet.2007.01.061

Cited by 295 publications

(98 citation statements)

References 134 publications

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“…A variety of reactive functional groups, such as 4-methoxycarbonyl and 4-acetyl amino groups, which are potentially suitable for further functionalization, survived in these reactions. (Table 2, entries [14][15]. Further experiments also demonstrated that sodium naphthalenesulfinates were also good substrates for this coupling reaction, as shown for the successful formation of 2-phenylnaphthalene and 1-phenylnaphthalene in 83% and 78% yields under the present reaction conditions, respectively ( Table 2, entries 16-17).…”

Section: Resultssupporting

confidence: 65%

“…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%

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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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Section: Resultssupporting

confidence: 65%

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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“…[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%

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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“…[46][47][48] Boronic acids often dimerize and trimerize to form boronic acid anhydrides and boroxines, 49) which make difficulties in the direct purification and determination of exact chemical amount. On the other hand, potassium organotrifluoroborates are highly air-and moisture-stable crystalline solids [50][51][52] and more easily prepared, purified, and handled although these compounds are less soluble in organic solvents and require protic solvents for their dissolution.…”

Section: Palladium-imidazolinium Carbene-catalyzed 12-addition Of Pomentioning

confidence: 99%

“…On the other hand, potassium organotrifluoroborates are highly air-and moisture-stable crystalline solids [50][51][52] and more easily prepared, purified, and handled although these compounds are less soluble in organic solvents and require protic solvents for their dissolution. [46][47][48] In spite of these advantages, only two kinds of rhodium(I)-phosphine catalysts for the 1,2-addition to aldehydes with potassium organotrifluoroborates have been reported. 53,54) Because the palladium/thioether-imidazolinium chloride system had high tolerance for water, it was expected to be a suitable catalyst system for this type of reagent.…”

Section: Palladium-imidazolinium Carbene-catalyzed 12-addition Of Pomentioning

confidence: 99%

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

Kuriyama

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Effective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.

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Recent advances in organotrifluoroborates chemistry

Cited by 295 publications

References 134 publications

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

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

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

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

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