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Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins.
Chemistry 2009; 15(24):5950-5C

Abstract

Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.

Authors+Show Affiliations

The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus, Denmark.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19418516

Citation

Gøgsig, Thomas M., et al. "Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-coupling Reactions With Electron-rich Olefins." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 24, 2009, pp. 5950-5.
Gøgsig TM, Lindhardt AT, Dekhane M, et al. Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins. Chemistry. 2009;15(24):5950-5.
Gøgsig, T. M., Lindhardt, A. T., Dekhane, M., Grouleff, J., & Skrydstrup, T. (2009). Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(24), pp. 5950-5. doi:10.1002/chem.200900313.
Gøgsig TM, et al. Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-coupling Reactions With Electron-rich Olefins. Chemistry. 2009 Jun 8;15(24):5950-5. PubMed PMID: 19418516.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins. AU - Gøgsig,Thomas M, AU - Lindhardt,Anders T, AU - Dekhane,Mouloud, AU - Grouleff,Julie, AU - Skrydstrup,Troels, PY - 2009/5/7/entrez PY - 2009/5/7/pubmed PY - 2009/8/19/medline SP - 5950 EP - 5 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 24 N2 - Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19418516/Heteroaromatic_tosylates_as_electrophiles_in_regioselective_Mizoroki_Heck_coupling_reactions_with_electron_rich_olefins_ L2 - https://doi.org/10.1002/chem.200900313 DB - PRIME DP - Unbound Medicine ER -