2. Academic Validation
  3. Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility

Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility

  • J Org Chem. 2016 Nov 18;81(22):11312-11315. doi: 10.1021/acs.joc.6b02287.
Yun Ma 1,  Russell F Algera 1,  David B Collum 1
Affiliations

Affiliation

  • 1 Department of Chemistry and Chemical Biology, Cornell University , Baker Laboratory, Ithaca, New York 14853-1301, United States.
PMID: 27768310 DOI: 10.1021/acs.joc.6b02287
Abstract

The reactivities and chemoselectivities of sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) are compared with those of lithium diisopropylamide (LDA) in tetrahydrofuran (THF). Metalations of arenes, epoxides, ketones, hydrazones, dienes, and alkyl and vinyl halides are represented. The positive attributes of NaDA-DMEA include high solubility, stability, resistance to solvent decomposition, and ease of preparation. The high reactivities and chemoselectivities often complement those of LDA-THF.

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