Related Experiment Video
Updated: Sep 8, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki-Miyaura Reactions of Pharmaceutically
David C Blakemore1, Andre Shavnya1, Michael C Willis2
1Medicine Design, Pfizer Inc., Groton, Connecticut 06340, United States.
Abstract:
The well documented difficulties associated with direct (hetero)-arylation of aza-aromatics (e.g., azines) at the α-position to nitrogen led to a collaborative project between the Willis group at Oxford and the Medicine Design department at Pfizer with the aim of addressing this challenge. The result of this collaboration has been a series of reports detailing the development of 2-aza-aryl sulfinates, as well as related 2-aza-aryl sulfone derivatives, as efficient nucleophilic reagents in palladium-catalyzed coupling reactions with (hetero)-aryl halides. The developed chemistry is routinely used in the medicinal chemistry laboratories at Pfizer, and the patent literature now contains many examples of these methods being embraced across the pharmaceutical industry. Hundreds of pyridyl (and related heterocyclic) sulfinates are now commercially available from multiple vendors. In this microperspective we discuss the development and evolution of these methods and highlight subsequent applications.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Preparation and Reactions of Sulfides
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Crossed Aldol Reaction Using Weak Bases
Hydroboration-Oxidation of Alkenes
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene