Selection of boron reagents for Suzuki–Miyaura coupling

AJJ Lennox, GC Lloyd-Jones - Chemical Society Reviews, 2014 - pubs.rsc.org
Suzuki–Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal
catalysed carbon–carbon bond forming reaction to date. Its success originates from a …

Organoboron compounds

N Miyaura - Cross-Coupling Reactions: A Practical Guide, 2002 - Springer
Until recently, organoboronic acids had found limited use in organic synthesis due to their
low reactivity for ionic reactions. However, it became increasingly clear that they are a …

Protodeboronation of heteroaromatic, vinyl, and cyclopropyl boronic acids: pH–rate profiles, autocatalysis, and disproportionation

PA Cox, AG Leach, AD Campbell… - Journal of the …, 2016 - ACS Publications
pH–rate profiles for aqueous–organic protodeboronation of 18 boronic acids, many widely
viewed as unstable, have been studied by NMR and DFT. Rates were pH-dependent, and …

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 …

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 …

Unlocking the potential of high-throughput experimentation for electrochemistry with a standardized microscale reactor

J Rein, JR Annand, MK Wismer, J Fu, JC Siu… - ACS Central …, 2021 - ACS Publications
Organic electrochemistry has emerged as an enabling and sustainable technology in
modern organic synthesis. Despite the recent renaissance of electrosynthesis, the broad …

Palladium-catalyzed Suzuki− Miyaura cross-coupling reactions of potassium aryl-and heteroaryltrifluoroborates

GA Molander, B Biolatto - The Journal of Organic Chemistry, 2003 - ACS Publications
An extended study of the reactivity of potassium aryl-and heteroaryltrifluoroborates in Suzuki-
Miyaura cross-coupling reactions is presented. The coupling of aryl-and electron-rich …

Protodeboronation of (hetero) arylboronic esters: direct versus prehydrolytic pathways and self-/auto-catalysis

HLD Hayes, R Wei, M Assante… - Journal of the …, 2021 - ACS Publications
The kinetics and mechanism of the base-catalyzed hydrolysis (ArB (OR) 2→ ArB (OH) 2) and
protodeboronation (ArB (OR) 2→ ArH) of a series of boronic esters, encompassing eight …

Tetrakis (3, 5-bis (trifluoromethyl) phenyl) borate. Highly lipophilic stable anionic agent for solvent-extraction of cations.

H Nishida, N Takada, M Yoshimura, T Sonoda… - Bulletin of the Chemical …, 1984 - jlc.jst.go.jp
Tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate (TFPB) anion was highly lipophilic,
practically insoluble in water, and durable against acid and oxidants. Partition equilibria of …

Structure, properties, and preparation of boronic acid derivatives. Overview of their reactions and applications

DG Hall - Boronic acids: preparation and applications in …, 2005 - Wiley Online Library
Structurally, boronic acids are trivalent boron-containing organic compounds that possess
one alkyl substituent (ie, a C–B bond) and two hydroxyl groups to fill the remaining valences …