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Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water

Xiaohan Li, Karthik S. Iyer, Ruchita R. Thakore, David K. Leahy, J. Daniel Bailey* and Bruce H. Lipshutz*

*Takeda Pharmaceuticals, 35 Landsdowne Street, Cambridge, Massachusetts 02139; University of California, Santa Barbara, California 93106, USA, Email:,

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

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Reductive aminations of shelf-stable bisulfite addition compounds of aldehydes can be run under aqueous micellar catalysis conditions with readily available α-picolineborane as the stoichiometric hydride source. Recycling of the aqueous reaction medium is easily accomplished.

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Key Words

reductive amination, α-picolineborane, green chemistry

ID: J54-Y2021