Pd-PEPPSI

Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides

Peng Lei, Guangrong Meng, Yun Ling, Jie An, Michal Szostak

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Pd-PEPPSI-IPr serves as a highly reactive precatalyst in the direct Suzuki-Miyaura cross-coupling of amides. An array of amides can be cross-coupled with a range of arylboronic acids in very good yields using a single, operationally simple protocol. The studies described represent the first use of versatile PEPPSI type of Pd-NHC complexes as catalysts for the cross-coupling of amides by N-C bond activation. The method is user-friendly, since it employs a commercially available, air- and moisture-stable Pd-PEPPSI-IPr complex. Pd-PEPPSI-IPr provides a significant improvement over all current Pd/phosphane catalysts for amide N-C bond activation. Mechanistic studies provide insight into the reaction rates of Pd-NHC-catalyzed cross-coupling of different amides, with Pd-PEPPSI-IPr being particularly effective for the cross-coupling of N-Boc carbamates under the developed conditions.

Original languageEnglish (US)
Pages (from-to)6638-6646
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number13
DOIs
StatePublished - Jul 7 2017

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Amides
phosphine
Chemical activation
Catalysts
Carbamates
Reaction rates
Moisture
Acids
Air

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Lei, Peng ; Meng, Guangrong ; Ling, Yun ; An, Jie ; Szostak, Michal. / Pd-PEPPSI : Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 13. pp. 6638-6646.
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abstract = "Pd-PEPPSI-IPr serves as a highly reactive precatalyst in the direct Suzuki-Miyaura cross-coupling of amides. An array of amides can be cross-coupled with a range of arylboronic acids in very good yields using a single, operationally simple protocol. The studies described represent the first use of versatile PEPPSI type of Pd-NHC complexes as catalysts for the cross-coupling of amides by N-C bond activation. The method is user-friendly, since it employs a commercially available, air- and moisture-stable Pd-PEPPSI-IPr complex. Pd-PEPPSI-IPr provides a significant improvement over all current Pd/phosphane catalysts for amide N-C bond activation. Mechanistic studies provide insight into the reaction rates of Pd-NHC-catalyzed cross-coupling of different amides, with Pd-PEPPSI-IPr being particularly effective for the cross-coupling of N-Boc carbamates under the developed conditions.",
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Pd-PEPPSI : Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides. / Lei, Peng; Meng, Guangrong; Ling, Yun; An, Jie; Szostak, Michal.

In: Journal of Organic Chemistry, Vol. 82, No. 13, 07.07.2017, p. 6638-6646.

Research output: Contribution to journalArticle

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AU - Szostak, Michal

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