Oxidative Rearrangement of MIDA ( N -Methyliminodiacetic Acid) Boronates: Mechanistic Insights and Synthetic Applications

Herein we report that coordinative hemilability allows the MIDA ( -methyliminodiacetic acid) nitrogen to behave as a nucleophile and intramolecularly intercept palladium π-allyl intermediates. A mechanistic investigation indicates that this rearrangement proceeds through an S 2-like displacement at...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-01, Vol.23 (2), p.324-328
Main Authors: Kaldas, Sherif J, Tien, Chieh-Hung, Gomes, Gabriel Dos Passos, Meyer, Stephanie, Sirvinskas, Martynas, Foy, Hayden, Dudding, Travis, Yudin, Andrei K
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein we report that coordinative hemilability allows the MIDA ( -methyliminodiacetic acid) nitrogen to behave as a nucleophile and intramolecularly intercept palladium π-allyl intermediates. A mechanistic investigation indicates that this rearrangement proceeds through an S 2-like displacement at tetrasubstituted boron to furnish novel DABN boronates. Oxidative addition into the N-C bond of the DABN scaffold furnishes borylated π-allyl intermediates that can then be trapped with a variety of nucleophiles, including in a three-component coupling.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03823