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Bench‐Stable Sulfoxide‐Based Boronates: Preparation and Application in a Tandem Suzuki Reaction
Author(s) -
Čubiňák Marek,
Eigner Václav,
Tobrman Tomáš
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801000
Subject(s) - chemistry , tandem , suzuki reaction , reagent , base (topology) , nucleophile , dimethyl sulfoxide , boronic acid , sulfoxide , combinatorial chemistry , organic chemistry , catalysis , palladium , mathematical analysis , materials science , mathematics , composite material
A set of novel aromatic and heteroaromatic bench‐stable sulfoxide‐based boronates was prepared. The structure of the boronates was established by means of X‐ray crystallography, and the prepared boronates were successively used in Suzuki cross‐coupling reactions under different conditions. We also developed a tandem Suzuki reaction so that a base is generated during the nucleophilic addition of Grignard reagents to 4‐bromobenzaldehyde. The formed intermediates were smoothly coupled with the prepared boronates and the boronic acids under external base‐free conditions.