The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b03739.
- Experimental and spectral data (PDF)
2018年9月30日日曜日
2018年9月12日水曜日
Mn Mediated Amidation 2018
Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes
† Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland
‡ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Tianjin University, Tianjin 300072 , People’s Republic of China
J. Am. Chem. Soc., 2018, 140 (22), pp 6789–6792
DOI: 10.1021/jacs.8b03739
Publication Date (Web): May 18, 2018
Copyright © 2018 American Chemical Society
Abstract
Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.
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2018年9月11日火曜日
Fe Coupling in CPME
Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents
Department of Chemistry, University of Illinois, 245 Roger Adams Laboratory, 600 South Mathews Avenue, Urbana, Illinois 61801, United States
J. Org. Chem., 2013, 78 (24), pp 12593–12628
DOI: 10.1021/jo402246h
Publication Date (Web): November 20, 2013
Copyright © 2013 American Chemical Society
Abstract
The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition-metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate that enable the challenging oxidative addition to the C(sp3)–S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized in which a nitrogen “directing group” on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac)3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile.
Optimization studies, calibration tables, and 1H and 13C NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.
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