Mechanistic development and recent applications of the Chan–Lam amination

MJ West, JWB Fyfe, JC Vantourout… - Chemical …, 2019 - ACS Publications
Transition metal-mediated formation of C–N bonds is an essential synthetic methodology.
The discovery of the Chan–Lam amination provided a C–N bond forming process that was …

Beyond classical sulfone chemistry: metal-and photocatalytic approaches for C–S bond functionalization of sulfones

J Corpas, SH Kim-Lee, P Mauleón… - Chemical Society …, 2022 - pubs.rsc.org
The exceptional versatility of sulfones has been extensively exploited in organic synthesis
across several decades. Since the first demonstration in 2005 that sulfones can participate …

A multi-objective active learning platform and web app for reaction optimization

JAG Torres, SH Lau, P Anchuri… - Journal of the …, 2022 - ACS Publications
We report the development of an open-source experimental design via Bayesian
optimization platform for multi-objective reaction optimization. Using high-throughput …

Closed-loop optimization of general reaction conditions for heteroaryl Suzuki-Miyaura coupling

NH Angello, V Rathore, W Beker, A Wołos, ER Jira… - Science, 2022 - science.org
General conditions for organic reactions are important but rare, and efforts to identify them
usually consider only narrow regions of chemical space. Discovering more general reaction …

The origin of chalcogen-bonding interactions

DJ Pascoe, KB Ling, SL Cockroft - Journal of the American …, 2017 - ACS Publications
Favorable molecular interactions between group 16 elements have been implicated in
catalysis, biological processes, and materials and medicinal chemistry. Such interactions …

Spectroscopic studies of the Chan–Lam amination: A mechanism-inspired solution to boronic ester reactivity

JC Vantourout, HN Miras, A Isidro-Llobet… - Journal of the …, 2017 - ACS Publications
We report an investigation of the Chan–Lam amination reaction. A combination of
spectroscopy, computational modeling, and crystallography has identified the structures of …

Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides

CA Malapit, JR Bour, CE Brigham, MS Sanford - Nature, 2018 - nature.com
Abstract The Suzuki–Miyaura cross-coupling of organoboron nucleophiles with aryl halide
electrophiles is one of the most widely used carbon–carbon bond-forming reactions in …

Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion

PA Cox, M Reid, AG Leach, AD Campbell… - Journal of the …, 2017 - ACS Publications
Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso
protonation of the boronate as the mechanism for base-catalyzed protodeboronation of …

Aryl boronic esters are stable on silica gel and reactive under Suzuki–Miyaura coupling conditions

N Oka, T Yamada, H Sajiki, S Akai, T Ikawa - Organic Letters, 2022 - ACS Publications
A wide range of aryl boronic 1, 1, 2, 2-tetraethylethylene glycol esters [ArB (Epin) s] were
readily synthesized. Purifying aryl boronic esters by conventional silica gel chromatography …

The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations

XAF Cook, A de Gombert, J McKnight… - Angewandte …, 2021 - Wiley Online Library
Azine‐containing biaryls are ubiquitous scaffolds in many areas of chemistry, and efficient
methods for their synthesis are continually desired. Pyridine rings are prominent amongst …