TY - JOUR
T1 - Assessing the pKa-Dependent Activity of Hydroxyl Hydrogen Bond Donors in the Organocatalyzed Cycloaddition of Carbon Dioxide to Epoxides: Experimental and Theoretical Study
AU - Yingcharoen, Prapussorn
AU - Kongtes, Chutima
AU - Arayachukiat, Sunatda
AU - Suvarnapunya, Kittipong
AU - Vummaleti, Sai V. C.
AU - Wannakao, Sippakorn
AU - Cavallo, Luigi
AU - poater, albert
AU - D'Elia, Valerio
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: V.D.E. thanks the Thailand Research Fund (Grant No. RSA6080059) for funding this research. A.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN, the Generalitat de Catalunya for the project 2017SGR39 and EU for a FEDER fund (UNGI08-4E-003).
PY - 2018/11/26
Y1 - 2018/11/26
N2 - The development of hydrogen bond donors (HBDs) as catalytic moieties in the cycloaddition of carbon dioxide to epoxides is an active field of research to access efficient, inexpensive and sustainable metal-free systems for the conversion of carbon dioxide to useful chemicals. Thus far, no systematic attempt to correlate the activity of a diverse selection of HBDs to their physico-chemical properties has been undertaken. In this work, we investigate factors influencing the catalytic activity of hydroxyl HBDs from different chemical families under ambient conditions by considering the HBDs Brønsted acidity (expressed as pKa), the number of hydroxyls and structural aspects. As an effect, this study highlights the crucial role of the hydroxyl protons’ Brønsted acidity in determining the catalytic activity of the HBDs, identifies an ideal range for the hydroxyl HBDs proton acidity (9
AB - The development of hydrogen bond donors (HBDs) as catalytic moieties in the cycloaddition of carbon dioxide to epoxides is an active field of research to access efficient, inexpensive and sustainable metal-free systems for the conversion of carbon dioxide to useful chemicals. Thus far, no systematic attempt to correlate the activity of a diverse selection of HBDs to their physico-chemical properties has been undertaken. In this work, we investigate factors influencing the catalytic activity of hydroxyl HBDs from different chemical families under ambient conditions by considering the HBDs Brønsted acidity (expressed as pKa), the number of hydroxyls and structural aspects. As an effect, this study highlights the crucial role of the hydroxyl protons’ Brønsted acidity in determining the catalytic activity of the HBDs, identifies an ideal range for the hydroxyl HBDs proton acidity (9
UR - http://hdl.handle.net/10754/629474
UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201801093
UR - http://www.scopus.com/inward/record.url?scp=85057549632&partnerID=8YFLogxK
U2 - 10.1002/adsc.201801093
DO - 10.1002/adsc.201801093
M3 - Article
SN - 1615-4150
VL - 361
SP - 366
EP - 373
JO - Advanced Synthesis & Catalysis
JF - Advanced Synthesis & Catalysis
IS - 2
ER -