0000000001309649
AUTHOR
Daniel J. Pyle
Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions
The development of efficient methods for facilitating N-C(O) bond activation in amides is an important objective in organic synthesis that permits the manipulation of the traditionally unreactive amide bonds. Herein, we report a comparative evaluation of a series of cyclic amides as activating groups in amide N-C(O) bond cross-coupling. Evaluation of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings using Pd(II)-NHC and Pd-phosphine systems reveals the relative reactivity order of N-activating groups in Suzuki-Miyaura cross-coupling. The reactivity of activated phenolic esters and thioesters is evaluated for comparison in O-C(O) and S-C(O) cross-c…
CCDC 2082397: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Daniel J. Pyle, Elwira Bisz, Bażej Dziuk, Krzysztof Ejsmont, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2021|J.Org.Chem.|86|10455|doi:10.1021/acs.joc.1c01110