<i>cis</i>-Dihydroxylation of Unsaturated Potassium Alkyl- and Aryltrifluoroborates

Molander, Gary A.; Figueroa, Ruth

doi:10.1021/ol052549e

Cited by 93 publications

(57 citation statements)

References 32 publications

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“…They are known for undergoing a variety of transformations while keeping the appended carbon-boron bond intact [11][12][13]. Consequently, molecular complexity can be built into various functionalized core reagents, providing more diversity by which targeted molecular platforms can be constructed.…”

Section: Cross-coupling With Organotrifluoroboratesmentioning

confidence: 99%

Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling

Cavalcanti

Molander

2016

Top Curr Chem (Z)

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The traditional transition metal-catalyzed cross-coupling reaction, although well suited for C(sp2)-C(sp2) cross-coupling, has proven less amenable toward coupling of C(sp3)-hybridized centers, particularly using functional group tolerant reagents and reaction conditions. The development of photoredox/Ni dual catalytic methods for cross-coupling has opened new vistas for the construction of carbon-carbon bonds at C(sp3)-hybridized centers. In this chapter, a general outline of the features of such processes is detailed.

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Section: Cross-coupling With Organotrifluoroboratesmentioning

confidence: 99%

Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling

Cavalcanti

Molander

2016

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“…55 These more highly elaborated organotrifluoroborates are also excellent substrates for cross-coupling reactions with aryl and alkenyl halides (eqs 18-20).…”

Section: Organotrifluoroborates Molander and Ellismentioning

confidence: 99%

Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction

2007

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Organotrifluoroborates represent an alternative to boronic acids, boronate esters, and organoboranes for use in Suzuki-Miyaura and other transition-metal-catalyzed cross-coupling reactions. The trifluoroborate moiety is stable toward numerous reagents that are often problematic for other boron species. Consequently, remote functional groups within the organotrifluoroborates can be manipulated, while retaining the valuable carbon-boron bond.

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“…28 Dihydroxylation of the olefin generates the 1,2-diol and ultimately, the 4,5-disubstituted imidazole (Scheme 7). [36][37][38] Another procedure for synthesizing imidazole that has seen considerable use is the Van Leusen imidazole synthesis (Scheme 8). 39 This is one of the most effective strategies for synthesizing 1,5-disubstituted imidazole.…”

Section: Synthesis Of Imidazolesmentioning

confidence: 99%