A Facile Alkylation of Aryl Aldehyde Trisylhydrazones with Trialkylboranes

Kabalka, George W.; Maddox, John T.; Bogas, Ekaterini; Tejedor, David; Ross, Emily

doi:10.1080/00397919608003704

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Cited by 4 publications

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“…We recently reported the initial results of a study involving the alkylation of aryl aldehyde (arenesulfonyl)hydrazones using trialkylboranes to produce the corresponding alkanes or alcohols in excellent yields upon workup (Scheme ) . The oxidative reaction sequence is the equivalent of a 1,2-addition of a trialkylborane to a carbonyl.…”

Section: Introductionmentioning

confidence: 99%

Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes

et al. 1997

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(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.

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Section: Introductionmentioning

confidence: 99%