title: B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.
abstract: Carboranes are boron-rich molecules that can be functionalized through metal-catalyzed cross-coupling. Here, for the first time, we report the use of bromo-carboranes in palladium-catalyzed cross-coupling for efficient B-N, B-O, and unprecedented B-CN bond formation. In many cases bromo-carboranes outperform the traditionally utilized iodo-carborane species. This marked difference in reactivity is leveraged to circumvent multistep functionalization by directly coupling small nucleophiles (-OH, -NH2, and -CN) and multiple functional groups onto the boron-rich clusters.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Rafal M
authors.initials: RM
authors.lastname: Dziedzic
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Liban M A
authors.initials: LM
authors.lastname: Saleh
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Jonathan C
authors.initials: JC
authors.lastname: Axtell
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Joshua L
authors.initials: JL
authors.lastname: Martin
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Simone L
authors.initials: SL
authors.lastname: Stevens
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego , 9500 Gilman Drive, La Jolla, California 92093, United States.|Department of Chemistry, University of West Florida , 11000 University Parkway, Pensacola, Florida 32514, United States.
authors.forename: A Timothy
authors.initials: AT
authors.lastname: Royappa
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego , 9500 Gilman Drive, La Jolla, California 92093, United States.
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Spokoyny