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Pd/Cu-catalyzed C-H arylation of 1,3,4-thiadiazoles with (hetero)aryl iodides, bromides, and triflates.
J Org Chem. 2012 Oct 05; 77(19):8768-74.JO

Abstract

The direct C-H arylation of 1,3,4-thiadiazoles with a wide range of (hetero)aryl iodides, bromides, and triflates is described using a Pd/Cu-catalyzed protocol. The methodology is compatible with substrates possessing electron-donating or electron-withdrawing substituents and also tolerates sterically hindered aryl halides. The utility of the developed protocol is demonstrated by a one-pot C-H arylation-Suzuki coupling sequence.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Vachhani DD
Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001, Leuven, Belgium.
Sharma A
No affiliation info available
Van der Eycken E
No affiliation info available

MeSH

BromidesCatalysisCopperHydrocarbons, HalogenatedHydrogen BondingIodidesMolecular StructurePalladiumThiadiazoles

Pub Type(s)

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

Language

eng

PubMed ID

22957511

Citation

Vachhani, Dipak D., et al. "Pd/Cu-catalyzed C-H Arylation of 1,3,4-thiadiazoles With (hetero)aryl Iodides, Bromides, and Triflates." The Journal of Organic Chemistry, vol. 77, no. 19, 2012, pp. 8768-74.
Vachhani DD, Sharma A, Van der Eycken E. Pd/Cu-catalyzed C-H arylation of 1,3,4-thiadiazoles with (hetero)aryl iodides, bromides, and triflates. J Org Chem. 2012;77(19):8768-74.
Vachhani, D. D., Sharma, A., & Van der Eycken, E. (2012). Pd/Cu-catalyzed C-H arylation of 1,3,4-thiadiazoles with (hetero)aryl iodides, bromides, and triflates. The Journal of Organic Chemistry, 77(19), 8768-74. https://doi.org/10.1021/jo301401q
Vachhani DD, Sharma A, Van der Eycken E. Pd/Cu-catalyzed C-H Arylation of 1,3,4-thiadiazoles With (hetero)aryl Iodides, Bromides, and Triflates. J Org Chem. 2012 Oct 5;77(19):8768-74. PubMed PMID: 22957511.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd/Cu-catalyzed C-H arylation of 1,3,4-thiadiazoles with (hetero)aryl iodides, bromides, and triflates. AU - Vachhani,Dipak D, AU - Sharma,Abhishek, AU - Van der Eycken,Erik, Y1 - 2012/09/21/ PY - 2012/9/11/entrez PY - 2012/9/11/pubmed PY - 2013/3/2/medline SP - 8768 EP - 74 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 19 N2 - The direct C-H arylation of 1,3,4-thiadiazoles with a wide range of (hetero)aryl iodides, bromides, and triflates is described using a Pd/Cu-catalyzed protocol. The methodology is compatible with substrates possessing electron-donating or electron-withdrawing substituents and also tolerates sterically hindered aryl halides. The utility of the developed protocol is demonstrated by a one-pot C-H arylation-Suzuki coupling sequence. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22957511/Pd/Cu_catalyzed_C_H_arylation_of_134_thiadiazoles_with__hetero_aryl_iodides_bromides_and_triflates_ L2 - https://doi.org/10.1021/jo301401q DB - PRIME DP - Unbound Medicine ER -