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An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters.
Org Biomol Chem. 2013 Sep 28; 11(36):6013-22.OB

Abstract

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Qian C
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, PR China.
Chen J
No affiliation info available
Fu M
No affiliation info available
Zhu S
No affiliation info available
Chen WH
No affiliation info available
Jiang H
No affiliation info available
Zeng W
No affiliation info available

MeSH

Boronic AcidsCatalysisEstersIminesMolecular StructureOrganometallic CompoundsPalladium

Pub Type(s)

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

Language

eng

PubMed ID

23939012

Citation

Qian, Cheng, et al. "An Unusual 1,2-aryl Shift in Palladium-catalyzed Cross-coupling Ethoxycarbonylation of Arylboronic Acids With Α-iminoesters." Organic & Biomolecular Chemistry, vol. 11, no. 36, 2013, pp. 6013-22.
Qian C, Chen J, Fu M, et al. An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters. Org Biomol Chem. 2013;11(36):6013-22.
Qian, C., Chen, J., Fu, M., Zhu, S., Chen, W. H., Jiang, H., & Zeng, W. (2013). An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters. Organic & Biomolecular Chemistry, 11(36), 6013-22. https://doi.org/10.1039/c3ob41011k
Qian C, et al. An Unusual 1,2-aryl Shift in Palladium-catalyzed Cross-coupling Ethoxycarbonylation of Arylboronic Acids With Α-iminoesters. Org Biomol Chem. 2013 Sep 28;11(36):6013-22. PubMed PMID: 23939012.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters. AU - Qian,Cheng, AU - Chen,Jiayan, AU - Fu,Meiqin, AU - Zhu,Shiya, AU - Chen,Wen-Hua, AU - Jiang,Huanfeng, AU - Zeng,Wei, PY - 2013/8/14/entrez PY - 2013/8/14/pubmed PY - 2014/3/19/medline SP - 6013 EP - 22 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 11 IS - 36 N2 - The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/23939012/An_unusual_12_aryl_shift_in_palladium_catalyzed_cross_coupling_ethoxycarbonylation_of_arylboronic_acids_with_α_iminoesters_ L2 - https://doi.org/10.1039/c3ob41011k DB - PRIME DP - Unbound Medicine ER -