AN EFFECTIVE METHOD FOR FORMYLATION OF WEAKLY NUCLEOPHILIC ANILINES AND INDOLE
In the presence of a catalytic amount of active titanium(IV) salt or Yb(OTf)3, weakly nucleophilic anilines and indole react under mild conditions with formic acid or aqueous formic acid to afford respectively the corresponding formanilides and indole-3-carboxaldehyde in excellent yields using 4-trifluoromethylbenzoic anhydride as a coreagent.
A HIGHLY EFFICIENT AND GENERAL N-MONOMETHYLATION OF FUNCTIONALIZED PRIMARY AMINES VIA FORMYLATION -- BORANE:METHYL SULFIDE REDUCTION
Formylation of functionalized primary aromatic and aliphatic amines with acetic formic anhydride (AFA) followed by borane:methyl sulfide reduction in the same pot affords the corresponding N-methylamines in excellent isolated yields, uncontaminated by bis alkylation; the reaction sequence is applicable to even very weakly basic and sterically hindered amines.
Krishnamurthy, S.
p. 3315 - 3318
(2007/10/02)
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