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Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}2] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water
Version 1
: Received: 30 October 2023 / Approved: 31 October 2023 / Online: 31 October 2023 (06:08:04 CET)
How to cite:
Ostrowska, S.; Rogalski, S.; Pietraszuk, C. Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}2] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water. Preprints2023, 2023102004. https://doi.org/10.20944/preprints202310.2004.v1
Ostrowska, S.; Rogalski, S.; Pietraszuk, C. Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}2] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water. Preprints 2023, 2023102004. https://doi.org/10.20944/preprints202310.2004.v1
Ostrowska, S.; Rogalski, S.; Pietraszuk, C. Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}2] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water. Preprints2023, 2023102004. https://doi.org/10.20944/preprints202310.2004.v1
APA Style
Ostrowska, S., Rogalski, S., & Pietraszuk, C. (2023). Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}<sub>2</sub>] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water. Preprints. https://doi.org/10.20944/preprints202310.2004.v1
Chicago/Turabian Style
Ostrowska, S., Szymon Rogalski and Cezary Pietraszuk. 2023 "Copper-Free Sonogashira Cross-Coupling of Aryl Chlorides with (Hetero)arylacetylenes in the Presence of Ppm Molar Loadings of [{Pd(OH)Cl(NHC)}<sub>2</sub>] Complexes. Hydrogen Chloride as a Coupling Product. Co-catalytic Effect of Water" Preprints. https://doi.org/10.20944/preprints202310.2004.v1
Abstract
Aryl chlorides and bromides in the presence of NHC palladium hydroxo dimers of the type [{Pd(µ-OH)Cl(NHC)}2] (where NHC = IPr, SIPr, IMes, SIMes) undergo an efficient and selective Sonogashira cross-coupling with terminal acetylenes. For the coupling of 4-chlorotoluene with phenylacetylene TON = 560000 was observed. The procedure enables high-throughput and selective synthesis of a broad spectrum of unsymmetrically substituted 1,2-diarylacetylenes. Nearly a quantitative amount of HCl was detected within cross-coupling products. Water plays the role of the base and is regenerated in the process so that it does not have to be used in stoichiometric amounts (relative to the limiting reactant). Generation of the active Pd(0) complex proceeds via ethanol oxidation.
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
