α-Picoline-borane, 2-Methylpyridine borane, PICB

Product Manager

Sandra Forbes

Pic-BH3 is a highly stable solid capable of being stored without significant decomposition. It serves as a superior substitute for reductive aminations in methanol, water, or even solvent-free settings.

Recent Literature

A gentle yet effective one-pot method for reductive amination of aldehydes and ketones with amines, employing α-picoline-borane as the reducer and a trace of AcOH, is reported. The reaction has proven successful in MeOH, H2O, and neat conditions, marking the first time reductive amination has been achieved in water and neat conditions.
S. Sato, T. Sakamoto, E. Miyazawa, Y. Kikugawa, Tetrahedron, 2004, 60, 7899-7906.

DOI: 10.1016/j.tet.2004.06.045

For reductive aminations of aldehyde bisulfite adducts that are stable at room temperature, using readily available α-picoline-borane as the stoichiometric hydride source under aqueous micellar catalysis conditions is feasible. The aqueous reaction medium can be readily recycled.
X. Li, K. S. Iyer, R. R. Thakore, D. K. Leahy, J. D. Bailey, B. H. Lipshutz, Org. Lett., 2021, 23, 7205-7208.

DOI: 10.1021/acs.orglett.1c02604

Half-sandwich ruthenium complexes facilitate anti-Markovnikov hydration and reductive hydration of terminal alkynes under mild conditions. Propargylic alcohols can be transformed into 1,3-diols with high yields and preserved stereochemistry at the propargylic position. Additionally, this method can be adapted for formal anti-Markovnikov reductive amination and oxidative hydration reactions to produce linear amines and carboxylic acids, respectively.
M. Zeng, S. B. Herzon, J. Org. Chem., 2015, 80, 8604-8618.

DOI: 10.1021/acs.joc.5b01220

An efficient one-pot method for the direct reductive alkylation of hydrazine derivatives using α-picoline-borane has been developed, yielding various N-alkylhydrazine derivatives through precise adjustment of substrate and reagent equivalency. This method has been utilized in the synthesis of active pharmaceutical ingredients, such as isocarboxazid, for therapeutic drugs.
Y. Kawase, T. Yamagishi, J.-y. Kato, T. Kutsuma, T. Kataoka, T. Iwakuma, T. Yokomatsu, Synthesis, 2014, 46, 455-464.