Acyclic twisted amides

G Meng, J Zhang, M Szostak - Chemical reviews, 2021 - ACS Publications
In this contribution, we provide a comprehensive overview of acyclic twisted amides,
covering the literature since 1993 (the year of the first recognized report on acyclic twisted …

Twisted amides: from obscurity to broadly useful transition‐metal‐catalyzed reactions by N− C amide bond activation

C Liu, M Szostak - Chemistry–A European Journal, 2017 - Wiley Online Library
The concept of using amide bond distortion to modulate amidic resonance has been known
for more than 75 years. Two classic twisted amides (bridged lactams) ingeniously designed …

Amide C–N bonds activation by A new variant of bifunctional N-heterocyclic carbene

Y Cai, Y Zhao, K Tang, H Zhang, X Mo, J Chen… - Nature …, 2024 - nature.com
We report an organocatalyst that combines a triazolium N-heterocyclic carbene (NHC) with a
squaramide as a hydrogen-bonding donor (HBD), which can effectively catalyze the …

Chemistry of bridged lactams and related heterocycles

M Szostak, J Aube - Chemical reviews, 2013 - ACS Publications
The amide bond is one of the most important functional groups in chemistry and biology. 1
Due to the strong resonance interaction between nN and π* C O orbitals (Figure 1), 2 the …

Inelastic neutron scattering study of reline: shedding light on the hydrogen bonding network of deep eutectic solvents

CF Araujo, JAP Coutinho, MM Nolasco… - Physical Chemistry …, 2017 - pubs.rsc.org
The solids choline chloride and urea, mixed in a 1: 2 molar proportion, form the iconic deep
eutectic solvent “Reline”. A combination of computational and vibrational spectroscopy tools …

Reversible twisting of primary amides via ground state N–C (O) destabilization: highly twisted rotationally inverted acyclic amides

G Meng, S Shi, R Lalancette, R Szostak… - Journal of the …, 2018 - ACS Publications
Since the seminal studies by Pauling in 1930s, planarity has become the defining
characteristic of the amide bond. Planarity of amides has central implications for the …

“Amide resonance” correlates with a breadth of C− N rotation barriers

CR Kemnitz, MJ Loewen - Journal of the American Chemical …, 2007 - ACS Publications
Complete basis set calculations (CBS-QB3) were used to compute the CN rotation barriers
for acetamide and eight related compounds, including acetamide enolate and O-protonated …

Transition‐metal‐free activation of amides by N− C bond cleavage

G Li, M Szostak - The Chemical Record, 2020 - Wiley Online Library
The amide bond N− C activation represents a powerful strategy in organic synthesis to
functionalize the historically inert amide linkage. This personal account highlights recent …

Non-classical amide bond formation: Transamidation and amidation of activated amides and esters by selective N–C/O–C cleavage

G Li, M Szostak - Synthesis, 2020 - thieme-connect.com
In the past several years, tremendous advances have been made in non-classical routes for
amide bond formation that involve transamidation and amidation reactions of activated …

Ground-State Distortion in N-Acyl-tert-butyl-carbamates (Boc) and N-Acyl-tosylamides (Ts): Twisted Amides of Relevance to Amide N–C Cross-Coupling

R Szostak, S Shi, G Meng, R Lalancette… - The Journal of organic …, 2016 - ACS Publications
Amide N–C (O) bonds are generally unreactive in cross-coupling reactions employing low-
valent transition metals due to nN→ π* C O resonance. Herein we demonstrate that N-acyl …