Intertwined chemistry of hydroxyl hydrogen-bond donors, epoxides and isocyanates in the organocatalytic synthesis of oxazolidinones versus isocyanurates: rational catalytic investigation and mechanistic understanding

2020 ◽  
Vol 10 (16) ◽  
pp. 5544-5558
Author(s):  
Prapussorn Yingcharoen ◽  
Wuttichai Natongchai ◽  
Albert Poater ◽  
Valerio D' Elia
Keyword(s):  
Hydrogen Bond ◽  
Mechanistic Understanding ◽  
Hydroxyl Hydrogen ◽  
Hydrogen Bond Donors

The efficiency and chemoselectivity of the cycloaddition of isocyanates to epoxides to afford oxazolidinones were investigated using hydroxyl hydrogen-bond donors as organocatalysts.

scholarly journals Assessing the pKa -Dependent Activity of Hydroxyl Hydrogen Bond Donors in the Organocatalyzed Cycloaddition of Carbon Dioxide to Epoxides: Experimental and Theoretical Study

2018 ◽  
Vol 361 (2) ◽  
pp. 366-373 ◽  
Author(s):  
Prapussorn Yingcharoen ◽  
Chutima Kongtes ◽  
Sunatda Arayachukiat ◽  
Kittipong Suvarnapunya ◽  
Sai V. C. Vummaleti ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Hydrogen Bond ◽  
Theoretical Study ◽  
Dependent Activity ◽  
Hydroxyl Hydrogen ◽  
Hydrogen Bond Donors

Gold setting the “gold standard” among transition metals as a hydrogen bond acceptor – a theoretical investigation

2017 ◽  
Vol 46 (15) ◽  
pp. 4960-4967 ◽  
Author(s):  
Ferdinand Groenewald ◽  
Helgard G. Raubenheimer ◽  
Jan Dillen ◽  
Catharine Esterhuysen
Keyword(s):  
Hydrogen Bond ◽  
Transition Metals ◽  
Theoretical Investigation ◽  
Gold Standard ◽  
Hydrogen Bond Acceptor ◽  
Hydrogen Bond Donors

MP2/aug-cc-pVTZ-pp calculations show that the Au(i) atom of dimethylaurate behaves as a hydrogen-bond acceptor to a range of hydrogen-bond donors.

scholarly journals Anion-Abstraction Catalysis: The Cooperative Mechanism of α-Chloroether Activation by Dual Hydrogen-Bond Donors

ACS Catalysis ◽  
2016 ◽  
Vol 6 (7) ◽  
pp. 4616-4620 ◽  
Author(s):  
David D. Ford ◽  
Dan Lehnherr ◽  
C. Rose Kennedy ◽  
Eric N. Jacobsen
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bond Donors

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

ChemInform Abstract: Homoallylic Alcohols and Trichloroacetamides as Hydrogen Bond Donors for Directed Dihydroxylation.

ChemInform ◽  
2010 ◽  
Vol 33 (9) ◽  
pp. no-no
Author(s):  
Timothy J. Donohoe ◽  
Lee Mitchell ◽  
Michael J. Waring ◽  
Madeleine Helliwell ◽  
Andrew Bell ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Homoallylic Alcohols ◽  
Hydrogen Bond Donors

Pyridine-bridged bifunctional organocatalysts for the synthesis of cyclic carbonates from carbon dioxide

2019 ◽  
Vol 43 (7-8) ◽  
pp. 248-256
Author(s):  
Quan-Yao Liu ◽  
Lei Shi ◽  
Ning Liu
Keyword(s):  
Carbon Dioxide ◽  
Hydrogen Bond ◽  
Cycloaddition Reaction ◽  
Carboxyl Groups ◽  
Cyclic Carbonates ◽  
Reaction Conditions ◽  
Halide Anions ◽  
Simple Filtration ◽  
Hydrogen Bond Donors

Hydroxyl- and carboxyl-functionalized imidazolium halides are used as efficient bifunctional organocatalysts for the synthesis of cyclic carbonates from CO2 and epoxides under mild reaction conditions. Control experiments suggest that the cycloaddition reaction is realized by the combination of the nucleophilic halide anions with hydroxyl and carboxyl groups as hydrogen bond donors. Moreover, the bifunctional organocatalysts can be easily recycled five times by simple filtration; however, a loss of activity was observed.

scholarly journals Hydrogen bond donors and acceptors are generally depolarized in α‐helices as revealed by a molecular tailoring approach

2019 ◽  
Author(s):  
Hiroko X. Kondo ◽  
Ayumi Kusaka ◽  
Colin K. Kitakawa ◽  
Jinta Onari ◽  
Shusuke Yamanaka ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Molecular Tailoring ◽  
Hydrogen Bond Donors
Sign in / Sign up

Export Citation Format

Share Document