Direct Reductive Amination of Aldehydes and Ketones Using Phenylsilane: Catalysis by Dibutyltin Dichloride

Abstract

A procedure for direct reductive amination of aldehydes and ketones was developed which uses phenylsilane as a stoichiometric reductant and dibutyltin dichloride as a catalyst. Suitable amines included anilines and dialkylamines but not monoalkylamines.

References

Page 1

	Year	Citations
Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures<sup>1</sup> Ahmed F. Abdel‐Magid, Kenneth G. Carson, Bruce D. Harris, The Journal of Organic Chemistry Chemical EngineeringCross-coupling ReactionEngineeringAldehyde DehydrogenaseBiochemistry	1996	1.5K
B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Hydrosilation of Imines via Silyliminium Intermediates James M. Blackwell, Eric R. Sonmor, Tiziana Scoccitti, Organic Letters Inorganic ChemistryChemical EngineeringEngineeringBroad RangeSpectral Evidence	2000	344
Polymethylhydrosiloxane: a versatile reducing agent for organic synthesis Nicholas J. Lawrence, Mark D. Drew, Simon M. Bushell Journal of the Chemical Society Perkin Transactions 1 Organic Material ChemistryPolymer ChemistryEngineeringPhysicochemical AnalysisM. D. Drew	1999	244
A mild, pyridine-borane-based reductive amination protocol Mark D. Bomann, Ian C. Guch, Marcello DiMare The Journal of Organic Chemistry Molecular SciencesChemical MeasurementChemical AnalysisDonut IconAltmetric Attention Score	1995	152
The alcoholysis of hydrosilanes E. Lukevics, M. Dzintara Journal of Organometallic Chemistry Chemical EngineeringEngineeringPetrochemicalOrganic ChemistryChemistry	1985	141
Chemo- and Stereoselective Monobenzoylation of 1,2-Diols Catalyzed by Organotin Compounds Fumiaki Iwasaki, Toshihide Maki, Osamu Onomura, The Journal of Organic Chemistry Novel OrganocatalystsEngineeringHeterocyclicBiochemistryNatural Sciences	2000	126
One-Pot Reductive Amination of Conjugated Aldehydes and Ketones with Silica Gel and Zinc Borohydride Brindaban C. Ranu, Adinath Majee, Arunkanti Sarkar The Journal of Organic Chemistry Conjugated AldehydesChemical EngineeringEngineeringAltmetric Attention ScoreOne-pot Reductive Amination	1998	121
Reductive N-alkylation of amides, carbamates and ureas Daniel Dubé, Andrew A. Scholte Tetrahedron Letters EngineeringReductive N-alkylationOrganic ChemistrySynthetic ChemistryBiomolecular Engineering	1999	114
Novel triethylsilane mediated reductive N -alkylation of amines: improved synthesis of 1-(4-imidazolyl)methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors Bang‐Chi Chen, Joseph E. Sundeen, Peng Guo, Tetrahedron Letters Medicinal ChemistryNew Farnesyltransferase InhibitorsNovel TriethylsilaneNatural SciencesMedicine	2001	84
Chemoselective Reductive Amination of Aldehydes and Ketones by Dibutylchlorotin Hydride-HMPA Complex Toshihiro Suwa, Erika Sugiyama, Ikuya Shibata, Synthesis EngineeringOrganic ChemistryChemistryHeterocycle ChemistryTin Reagent	2000	56

Page 1