Related Experiment Video
Updated: May 17, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
One-pot C-N/C-C cross-coupling of methyliminodiacetic acid boronyl arenes enabled by protective enolization
Jonathan E Grob1, Michael A Dechantsreiter, Ritesh B Tichkule
1Novartis Institutes for BioMedical Research, Inc., 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Abstract:
Iterative cross-coupling is a highly efficient and versatile strategy for modular construction in organic synthesis, though this has historically been demonstrated solely in the context of C-C bond formation. A C-N cross-coupling of haloarene methyliminodiacetic acid (MIDA) boronates with a wide range of aromatic and aliphatic amines is reported. Successful cross-coupling of aliphatic amines was realized only through protective enolization of the MIDA group. This reaction paradigm was subsequently utilized to achieve a one-pot C-N/C-C cross-coupling sequence.
Related Concept Videos
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
α-Alkylation of Ketones via Enolate Ions
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Conjugate Addition of Enolates: Michael Addition

