Accessing Ambiphilic Phosphine Boronates through C-H Borylation by an Unforeseen Cationic Iridium Complex.

Autor: Wright SE; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Richardson-Solorzano S; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Stewart TN; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Miller CD; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Morris KC; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Daley CJA; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA., Clark TB; Department of Chemistry & Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, CA, 92110, USA.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Feb 25; Vol. 58 (9), pp. 2834-2838. Date of Electronic Publication: 2019 Jan 29.
DOI: 10.1002/anie.201812857
Abstrakt: Ambiphilic molecules, which contain a Lewis base and Lewis acid, are of great interest based on their unique ability to activate small molecules. Phosphine boronates are one class of these substrates that have interesting catalytic activity. Direct access to these phosphine boronates is described through the iridium-catalyzed C-H borylation of phosphines. An unconventional cationic iridium catalyst was identified as optimal for a range of phosphines, providing good yields and selectivity across a diverse class of phosphine boronates (isolated as the borane-protected phosphine). A complimentary catalyst system (quinoline-based silane ligand with [(COD)IrOMe] 2 ) was optimal for biphenyl-based phosphines. Selective polyborylation was also shown providing bis- and tris-borylated phosphines. Deprotection of the phosphine boronate provided free ambiphilic phosphine boronates, which do not have detectable interactions between the phosphorus and boron atoms in solution or the solid state.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
Externí odkaz: