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Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block
Abstract
This study represents the first example of a manganese-catalyzed environmentally benign, practical three-component aminomethylation of activated aromatic compounds including naphtols, phenols, pyridines, indoles, carbazoles, and thiophenes in combination with amines and MeOH as a C1 source. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps which give rise to selective C-C and C-N bond formations, thereby releasing hydrogen and water. A well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent behavior of isoelectronic Mn(I) and Fe(II) PNP pincer systems.
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Catalytic conversion of biomass to biofuels
Alonso, D. M., Bond, J. Q., & Dumesic, J. A. (2010) · Green Chemistry · doi:10.1039/c004654j · Cited by 2,333
Cited by
Manganese-Catalyzed Sequential Hydrogenation of CO2 to Methanol via Formamide
Kar, S., Goeppert, A., Kothandaraman, J., & Prakash, G. K. S. (2017) · ACS Catalysis · doi:10.1021/acscatal.7b02066 · Cited by 258
Metadata
- Authors
- Mastalir, M., Pittenauer, E., Allmaier, G., & Kirchner, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-06-21
- Volume
- 139
- Issue
- 26
- Pages
- 8812-8815
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2681819057
- Cited by
- 198
- References
- 1
- FWCI
- 10.65
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mastalir, M., Pittenauer, E., Allmaier, G., & Kirchner, K. (2017). Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.7b05253
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