Amide directed iridium C(sp 3 )-H borylation catalysis with high N -methyl selectivity.

Autor: Dannatt JE; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, MI, 48824-1322, USA.; Department of Chemistry, University of Dallas, 1845 East Northgate Drive, Irving, TX, 75062, USA., Yadav A; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, MI, 48824-1322, USA., Smith MR 3rd; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, MI, 48824-1322, USA., Maleczka RE Jr; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, MI, 48824-1322, USA.
Jazyk: angličtina
Zdroj: Tetrahedron [Tetrahedron] 2022 Mar 12; Vol. 109. Date of Electronic Publication: 2021 Nov 26.
DOI: 10.1016/j.tet.2021.132578
Abstrakt: A bidentate monoanionic ligand system was developed to enable iridium catalyzed C(sp 3 )-H activation borylation of N -methyl amides. Borylated amides were obtained in moderate to good isolated yields, and exclusive mono-borylation allowed the amide to be the limiting reagent. Selectivity for C(sp 3 )-H activation was demonstrated in the presence of sterically available C(sp 3 )-H bonds. Competitive kinetic isotope studies revealed a large primary isotope effect, implicating C-H activation as the rate limiting step.
Competing Interests: Declaration of competing interest M.R.S. and R.E.M. own a percentage of BoroPharm, Inc.
Databáze: MEDLINE
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