Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2

A Catalytic and Mechanistic Study

Arup Mukherjee, Alexander Nerush, Gregory Leitus, Linda J W Shimon, Yehoshoa Ben David, Noel Angel Espinosa Jalapa, David Milstein

Research output: Contribution to journal › Article

170 Citations (Scopus)

Abstract

The catalytic dehydrogenative coupling of alcohols and amines to form aldimines represents an environmentally benign methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts. We present the dehydrogenative coupling of alcohols and amines to form imines and H2 that is catalyzed, for the first time, by a complex of the earth-abundant Mn. Detailed mechanistic study was carried out with the aid of NMR spectroscopy, intermediate isolation, and X-ray analysis.

Original languageEnglish
Pages (from-to)4298-4301
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number13
DOIs
Publication statusPublished - Apr 20 2016

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Manganese
Amines
Alcohols
Organic Chemistry
Imines
X ray analysis
Precious metals
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Metals
Earth (planet)
X-Rays
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2 : A Catalytic and Mechanistic Study. / Mukherjee, Arup; Nerush, Alexander; Leitus, Gregory; Shimon, Linda J W; Ben David, Yehoshoa; Espinosa Jalapa, Noel Angel; Milstein, David.

In: Journal of the American Chemical Society, Vol. 138, No. 13, 20.04.2016, p. 4298-4301.

Research output: Contribution to journal › Article

Mukherjee, A, Nerush, A, Leitus, G, Shimon, LJW, Ben David, Y, Espinosa Jalapa, NA & Milstein, D 2016, 'Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2: A Catalytic and Mechanistic Study', Journal of the American Chemical Society, vol. 138, no. 13, pp. 4298-4301. https://doi.org/10.1021/jacs.5b13519
Mukherjee A, Nerush A, Leitus G, Shimon LJW, Ben David Y, Espinosa Jalapa NA et al. Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2: A Catalytic and Mechanistic Study. Journal of the American Chemical Society. 2016 Apr 20;138(13):4298-4301. https://doi.org/10.1021/jacs.5b13519
Mukherjee, Arup ; Nerush, Alexander ; Leitus, Gregory ; Shimon, Linda J W ; Ben David, Yehoshoa ; Espinosa Jalapa, Noel Angel ; Milstein, David. / Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2 : A Catalytic and Mechanistic Study. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 13. pp. 4298-4301.
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