0000000001299862
AUTHOR
Md. Mahbubur Rahman
N-Acyl-glutarimides: Effect of Glutarimide Ring on the Structures of Fully Perpendicular Twisted Amides and N–C Bond Cross-Coupling
N-Acyl-glutarimides have emerged as the most reactive precursors for N-C(O) bond cross-coupling reactions to date, wherein the reactivity is driven by ground-state destabilization of the amide bond. Herein, we report a full study on the effect of a glutarimide ring on the structures, electronic properties, and reactivity of fully perpendicular N-acyl-glutarimide amides. Most notably, this report demonstrates the generality of deploying N-acyl-glutarimides to achieve full twist of the acyclic amide bond, and results in the discovery of N-acyl-glutarimide amide with an almost perfect twist value, τ = 89.1°. X-ray structures of five new N-acyl-glutarimides are reported. Reactivity studies in t…
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 1969088: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Chengwei Liu, Elwira Bisz, Błażej Dziuk, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2020|J.Org.Chem.|85|5475|doi:10.1021/acs.joc.0c00227
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
CCDC 1969085: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Chengwei Liu, Elwira Bisz, Błażej Dziuk, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2020|J.Org.Chem.|85|5475|doi:10.1021/acs.joc.0c00227
CCDC 1969087: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Chengwei Liu, Elwira Bisz, Błażej Dziuk, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2020|J.Org.Chem.|85|5475|doi:10.1021/acs.joc.0c00227
CCDC 1969082: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Chengwei Liu, Elwira Bisz, Błażej Dziuk, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2020|J.Org.Chem.|85|5475|doi:10.1021/acs.joc.0c00227
CCDC 1969086: Experimental Crystal Structure Determination
Related Article: Md. Mahbubur Rahman, Chengwei Liu, Elwira Bisz, Błażej Dziuk, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak, Michal Szostak|2020|J.Org.Chem.|85|5475|doi:10.1021/acs.joc.0c00227