» Articles » PMID: 28144357

New Approaches to Organocatalysis Based on C-H and C-X Bonding for Electrophilic Substrate Activation

Overview
Specialty Chemistry
Date 2017 Feb 2
PMID 28144357
Citations 10
Authors
Affiliations
Soon will be listed here.
Abstract

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.

Citing Articles

Trialkylphosphonium oxoborates as C(sp)-H oxyanion holes and their application in catalytic chemoselective acetalization.

Leung V, Wong H, Pook C, Steve Tse Y, Yeung Y Chem Sci. 2023; 14(44):12684-12692.

PMID: 38020391 PMC: 10646966. DOI: 10.1039/d3sc03081d.


Main Group Molecular Switches with Swivel Bifurcated to Trifurcated Hydrogen Bond Mode of Action.

Hum G, Phang S, Ong H, Leon F, Quek S, Khoo Y J Am Chem Soc. 2023; 145(23):12475-12486.

PMID: 37267593 PMC: 10273318. DOI: 10.1021/jacs.2c12713.


Structure-Directing Interplay between Tetrel and Halogen Bonding in Co-Crystal of Lead(II) Diethyldithiocarbamate with Tetraiodoethylene.

Zelenkov L, Ivanov D, Tyumentsev I, Izotova Y, Kukushkin V, Bokach N Int J Mol Sci. 2022; 23(19).

PMID: 36233178 PMC: 9569466. DOI: 10.3390/ijms231911870.


Metal Centers as Nucleophiles: Oxymoron of Halogen Bond-Involving Crystal Engineering.

Ivanov D, Bokach N, Kukushkin V, Frontera A Chemistry. 2021; 28(2):e202103173.

PMID: 34623005 PMC: 9298210. DOI: 10.1002/chem.202103173.


Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp-Hybridized Carbon-Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold.

Uno H, Matsuzaki K, Shiro M, Shibata N Molecules. 2020; 25(19).

PMID: 33022984 PMC: 7583727. DOI: 10.3390/molecules25194539.


References
1.
Zabka M, Sebesta R . Experimental and Theoretical Studies in Hydrogen-Bonding Organocatalysis. Molecules. 2015; 20(9):15500-24. PMC: 6331831. DOI: 10.3390/molecules200915500. View

2.
Brown A, Beer P . Halogen bonding anion recognition. Chem Commun (Camb). 2016; 52(56):8645-58. DOI: 10.1039/c6cc03638d. View

3.
Sarwar M, Dragisic B, Salsberg L, Gouliaras C, Taylor M . Thermodynamics of halogen bonding in solution: substituent, structural, and solvent effects. J Am Chem Soc. 2010; 132(5):1646-53. DOI: 10.1021/ja9086352. View

4.
Hay B, Bryantsev V . Anion-arene adducts: C-H hydrogen bonding, anion-pi interaction, and carbon bonding motifs. Chem Commun (Camb). 2008; (21):2417-28. DOI: 10.1039/b800055g. View

5.
Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G . The Halogen Bond. Chem Rev. 2016; 116(4):2478-601. PMC: 4768247. DOI: 10.1021/acs.chemrev.5b00484. View