Pinacolborane as the boron source in nitrogen-directed borylations of aromatic N,N-dimethylhydrazones.
A mild procedure for the Ir(III)-catalyzed nitrogen-directed ortho borylation of aromatic N,N-dialkylhydrazones using pinacolborane as the boron source has been developed. The methodology relies on a modified, hemilabile N,N ligand built on a 4-N,N-dimethylaminopyridine unit that provides high reactivity while maintaining exclusive ortho-selectivity. This procedure can be combined with Suzuki-Miyaura cross-couplings in a 'one-pot' fashion to afford functionalized biaryl derivatives that, upon subsequent 'one-pot', high yielding transformations, provide a convenient entry for the preparation of advanced benzonitrile intermediates for the synthesis of Sartan-type drugs.
Instituto de Investigaciones Químicas (IIQ), CSIC/US, Américo Vespucio 49, 41092 Sevilla, Spain.
Rocío
R
López-Rodríguez
Abel
A
Ros
Rosario
R
Fernández
José M
JM
Lassaletta
D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D008744:Methylamines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
C578864:4,4,5,5-tetramethyl(1,3,2)dioxaborolane; C578863:4-N,N-dimethylaminopyridine; D001896:Boron Compounds; D006835:Hydrazones; D008744:Methylamines; D009570:Nitriles; D011725:Pyridines; D007495:Iridium; C014356:benzonitrile; D009584:Nitrogen; D001895:Boron