Formation of tertiary amides and dihydrogen by dehydrogenative coupling of primary alcohols with secondary amines catalyzed by ruthenium bipyridine-based pincer complexes

Dipankar Srimani, Ekambaram Balaraman, Peng Hu, Yehoshoa Ben-David, David Milstein

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Dehydrogenative coupling of primary alcohols with secondary amines to form tertiary amides and dihydrogen (H2) is efficiently catalyzed by bipyridyl-based ruthenium pincer complexes (0.2-1 mol%) under neutral conditions (in case of the dearomatized complexes), or with added catalytic amount of base. The reaction is sensitive to steric hindrance; in the case of amidation of bulky secondary amines a less sterically hindered complex is more efficient. Selective acylation of primary amines in the presence of secondary amines was also demonstrated.

Original languageEnglish
Pages (from-to)2525-2530
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number13
DOIs
Publication statusPublished - Sep 16 2013

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Ruthenium
Amides
Amines
Alcohols
Acylation
2,2'-Dipyridyl

Keywords

  • alcohols
  • amidation
  • amines
  • dehydrogenation
  • oxidative coupling
  • ruthenium pincer complexes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Formation of tertiary amides and dihydrogen by dehydrogenative coupling of primary alcohols with secondary amines catalyzed by ruthenium bipyridine-based pincer complexes. / Srimani, Dipankar; Balaraman, Ekambaram; Hu, Peng; Ben-David, Yehoshoa; Milstein, David.

In: Advanced Synthesis and Catalysis, Vol. 355, No. 13, 16.09.2013, p. 2525-2530.

Research output: Contribution to journalArticle

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AU - Ben-David, Yehoshoa

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