@article{0f07124233c24e98838eecbeac5d3ba4,
title = "Potassium trimethylsilanolate enables rapid, homogeneous suzuki-miyaura cross-coupling of boronic esters",
abstract = "Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.",
keywords = "Cross-coupling, Homogeneous catalysis, Palladium, Suzuki-miyaura reaction, Synthetic methods",
author = "Delaney, {Connor P.} and Kassel, {Vincent M.} and Denmark, {Scott E.}",
note = "Funding Information: We are grateful to the National Institutes of Health (Grant GM R35 127010) for generous financial support. We also thank the UIUC SCS support facilities (microanalysis, mass spectrometry, and NMR spectroscopy) for their assistance. Dr. Gerald Larson (Gelest) is thanked for a generous gift of TMSOK. We also acknowledge Dr. Andy A. Thomas for obtaining rate profiles for the boronic acid, glycol ester, neopentyl ester, and pinacol ester in our initial investigations. During the processing of this manuscript, two related papers appeared in ACS Catalysis (DOI: 10.1021/acscatal.9b03667 and 10.1021/acscatal.9b03666 ), which also describe anhydrous, base-activated Suzuki−Miyaura cross-couplings albeit at significantly higher temperatures than we report. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",
year = "2020",
month = jan,
day = "3",
doi = "10.1021/acscatal.9b04353",
language = "English (US)",
volume = "10",
pages = "73--80",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "1",
}