Functionalization of organotrifluoroborates: reductive amination.

The Journal of Organic Chemistry
Gary A Molander, David J Cooper

Abstract

Herein we report the conversion of aldehyde-containing potassium and tetrabutylammonium organotrifluoroborates to the corresponding amines through reductive amination protocols. Potassium formate facilitated by catalytic palladium acetate, sodium triacetoxyborohydride, and pyridine borane have all served as effective hydride donors, reducing the initially formed imines or iminium ions to provide the corresponding amines.

References

Feb 22, 2002·The Journal of Organic Chemistry·Thierry Billard, Bernard R Langlois
May 24, 2003·The Journal of Organic Chemistry·Gary A Molander, Betina Biolatto
Jun 9, 2004·Chembiochem : a European Journal of Chemical Biology·Toru AsanoYoshinori Yamamoto
Sep 17, 2004·Chemistry : a European Journal·Luca FrullanoJoop A Peters
Oct 14, 2005·Journal of the American Chemical Society·Gary A Molander, María Ribagorda
Dec 31, 2005·Organic Letters·Gary A Molander, Ruth Figueroa
Jan 26, 2006·Bioorganic & Medicinal Chemistry Letters·Mimi L QuanRuth R Wexler
Jul 14, 2006·Organic Letters·Chris SchwartzPatrick H Dussault
Jul 29, 2006·The Journal of Organic Chemistry·Gary A Molander, Ruth Figueroa
Sep 9, 2006·The Journal of Organic Chemistry·Gary A Molander, Noel M Ellis
Jan 30, 2007·Accounts of Chemical Research·Gary A Molander, Noel Ellis
Apr 6, 2007·The Journal of Organic Chemistry·Gary A Molander, David J Cooper
Nov 23, 2007·Journal of the American Chemical Society·Sandra Lee, David W C MacMillan

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Citations

Jan 5, 2011·The Journal of Organic Chemistry·Gary A Molander, Livia N Cavalcanti
Aug 5, 2011·The Journal of Organic Chemistry·Gary A Molander, Livia N Cavalcanti
Sep 12, 2009·The Journal of Organic Chemistry·Gary A MolanderLauren E Kennedy
Aug 10, 2012·Organic Letters·Gary A Molander, Kehinde Ajayi
Aug 12, 2014·Contrast Media & Molecular Imaging·Benjamin P BurkeStephen J Archibald
Oct 6, 2012·Angewandte Chemie·Zhi HeAndrei K Yudin
Oct 5, 2013·Chemical Society Reviews·Alastair J J Lennox, Guy C Lloyd-Jones
Jul 21, 2017·Angewandte Chemie·Marian RauserMeike Niggemann
Sep 19, 2014·ACS Chemical Biology·Viachaslau BernatNuska Tschammer
Nov 10, 2018·Journal of the American Chemical Society·Tim MarkovicMichael C Willis

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