TY - JOUR
T1 - Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium-Bis(silyl)xanthene Complex
T2 - Application to One-Pot Synthesis of Diarylamines and N-Arylimines
AU - Kitano, Takeo
AU - Komuro, Takashi
AU - Tobita, Hiromi
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grants JP25410058, JP15H03782, and JP16K05714 from the Japan Society for the Promotion of Science (JSPS). We also acknowledge the Research and Analytical Center for Giant Molecules, Tohoku University, for mass spectroscopic measurements and elemental analysis.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/4/8
Y1 - 2019/4/8
N2 - A ruthenium complex bearing a bis(silyl)xanthene chelate ligand xantsil, i.e. Ru[κ 3 (Si,O,Si)-xantsil](CO)(PCyp 3 ) (1a, Cyp = cyclopentyl), was found to catalyze both double and single hydroboration reactions of nitriles with pinacolborane (HBpin) and 9-borabicyclo[3.3.1]nonane (9-BBN) to give bis(boryl)amines 2 and N-borylimines 3, respectively, in mostly >99% yields. By combination of these reactions with subsequent palladium-catalyzed deborylative C-N coupling reactions of 2 and 3 with a 1:1 mixture of bromoarenes and KO t Bu, one-pot synthetic routes to tertiary N,N-diarylamines 4 and N-arylaldimines 5 from nitriles were developed.
AB - A ruthenium complex bearing a bis(silyl)xanthene chelate ligand xantsil, i.e. Ru[κ 3 (Si,O,Si)-xantsil](CO)(PCyp 3 ) (1a, Cyp = cyclopentyl), was found to catalyze both double and single hydroboration reactions of nitriles with pinacolborane (HBpin) and 9-borabicyclo[3.3.1]nonane (9-BBN) to give bis(boryl)amines 2 and N-borylimines 3, respectively, in mostly >99% yields. By combination of these reactions with subsequent palladium-catalyzed deborylative C-N coupling reactions of 2 and 3 with a 1:1 mixture of bromoarenes and KO t Bu, one-pot synthetic routes to tertiary N,N-diarylamines 4 and N-arylaldimines 5 from nitriles were developed.
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U2 - 10.1021/acs.organomet.9b00064
DO - 10.1021/acs.organomet.9b00064
M3 - Article
AN - SCOPUS:85062873953
VL - 38
SP - 1417
EP - 1420
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 7
ER -