Palladium-Catalyzed Cross-Coupling Reactions of Potassium N-Methyltrifluoroborate Isoindolin-1-one with Aryl and Heteroaryl Chlorides

Nadaf, Rashid N.; Seapy, Dave G.

doi:10.1080/00397911.2014.884591

Cited by 5 publications

(2 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Amine derivatives have also been prepared directly in this manner, introducing added efficiency into the overall process because the entire functional unit can be incorporated directly rather than initially introducing the amine with subsequent amine functionalization in a separate step. Thus, amidomethyltrifluoroborates (eq ), Boc-protected (1° and 2°) aminomethyltrifluoroborates (eqs and 40), sulfonamidomethyltrifluoroborates (eq 41), N -trifluoroboratomethylisoindolin-1-ones (eq 42), and imidomethyltrifluoroborates have all been prepared and cross-coupled effectively with a variety of aryl electrophiles, including halides, various sulfonates, ,,,, and sulfamates (eq 43). …”

Section: Palladium-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Organotrifluoroborates: Another Branch of the Mighty Oak

2015

View full text Add to dashboard Cite

Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules. Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure. Currently >600 structurally diverse reagents of this class are commercially available, and >850 such compounds have been reported from the author's laboratory. The organotrifluoroborates can be utilized as shelf-stable precursors to a variety of end products through simple functional group transformations and have also been employed as partners in cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or individual formats. Within the realm of cross-coupling reactions, organotrifluoroborates provide a practical entry to substructural entities not readily accessed using other organometallic reagents, and most recently, the development of a novel mechanistic paradigm for cross-coupling promises to expand the range of accessible cross-coupling partners even further to include both single- and two-electron processes.

show abstract

Section: Palladium-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Organotrifluoroborates: Another Branch of the Mighty Oak

2015

View full text Add to dashboard Cite

show abstract

“…This protocol could be utilized in the construction of optically active drugs from optically active alkylboron compounds. Nadaf et al 132 described the palladium-catalyzed Suzuki–Miyaura cross-coupling reactions between newly synthesized potassium N -methyltrifluoroborate isoindolin-1-one ( 77 ) and aryl and heteroaryl chlorides to prepare libraries of substituted N -benzyl isoindolin-1-ones 78 (Scheme 26 ).…”

Section: Pd-catalyzed Reactionsmentioning

confidence: 99%

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

Kumar,

Jyoti

et al. 2023

SynOpen

View full text Add to dashboard Cite

During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date.1 Introduction2 Pd-Catalyzed Reactions2.1 C–C Cross-Coupling Reactions2.2 C–N Cross-Coupling Reactions2.3 C–P Cross-Coupling Reactions3 Ni-Catalyzed Cross-Coupling Reactions3.1 C–C Cross-Coupling Reactions4 Cu-Catalyzed Cross-Coupling Reactions4.1 C–C Cross-Coupling Reactions4.2 C–O Cross-Coupling Reactions4.2 C–N Cross-Coupling Reactions4.4 C–P Cross-Coupling Reactions4.5 C–Se Cross-Coupling Reactions4.6 C–S Cross-Coupling Reactions5 Fe-Catalyzed Reactions5.1 C–C Cross-Coupling Reactions5.2 C–S Cross-Coupling Reactions6 Co-Catalyzed Reactions7 Transition-Metal Nanoparticle-Promoted Reactions7.1 Pd Nanoparticles7.2 Cu Nanoparticles8 Miscellaneous Reactions9 Perspectives and Future Directions

show abstract

The Chemistry of Organotrifluoroborates

Cavalcanti

Molander

2019

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

Organotrifluoroborates have emerged as among the most versatile class of organoboron reagents for elaboration of complex organic molecules. They are air‐ and moisture‐stable crystalline solids or free‐flowing powders that can be easily prepared and stored on the bench for years without decomposition. Furthermore, the tetra‐coordinated nature of organotrifluoroborates engenders unique reactivity patterns complementary to those of the tri‐coordinated organoboron species. Over the years, organotrifluoroborates have been employed in myriad reactions for carbon–carbon and carbon–heteroatom bond formation, showing the importance of these compounds for synthetic organic chemistry. Herein described is an overview of the synthesis and application of organotrifluoroborates in a vast array of organic transformations.

show abstract

Palladium-Catalyzed Cross-Coupling Reactions of Potassium N-Methyltrifluoroborate Isoindolin-1-one with Aryl and Heteroaryl Chlorides

Cited by 5 publications

References 21 publications

Organotrifluoroborates: Another Branch of the Mighty Oak

Organotrifluoroborates: Another Branch of the Mighty Oak

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

The Chemistry of Organotrifluoroborates

Contact Info

Product

Resources

About