Journal
ORGANIC LETTERS
Volume 6, Issue 4, Pages 637-640Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol036480r
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- NIGMS NIH HHS [R01-GM67187] Funding Source: Medline
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Trifluoroacetyl derivatives of hydrazines undergo clean and efficient reductive cleavage of the N-N bond with SmI2 in the presence of MeOH. After N-trifluoroacetylation, acyl-, aryl-, and alkyl-substituted hydrazines are reductively cleaved by this method to afford trifluoroacetamides in yields ranging from 70 to 96%. These conditions accommodate alkene functionality, avoid racemization, and furnish chiral amines bearing a readily removable TFA protecting group.
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