Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes

被引:0
作者
Saravanakumar Elangovan
Jacob Neumann
Jean-Baptiste Sortais
Kathrin Junge
Christophe Darcel
Matthias Beller
机构
[1] Leibniz-Institut für Katalyse e.V. an der Universität Rostock,
[2] UMR 6226 CNRS—Université de Rennes 1 Institut des Sciences Chimiques de Rennes,undefined
[3] Team Organometallics: Materials and Catalysis—Centre for Catalysis and Green Chemistry,undefined
来源
Nature Communications | / 7卷
关键词
D O I
暂无
中图分类号
学科分类号
摘要
Borrowing hydrogen (or hydrogen autotransfer) reactions represent straightforward and sustainable C–N bond-forming processes. In general, precious metal-based catalysts are employed for this effective transformation. In recent years, the use of earth abundant and cheap non-noble metal catalysts for this process attracted considerable attention in the scientific community. Here we show that the selective N-alkylation of amines with alcohols can be catalysed by defined PNP manganese pincer complexes. A variety of substituted anilines are monoalkylated with different (hetero)aromatic and aliphatic alcohols even in the presence of other sensitive reducible functional groups. As a special highlight, we report the chemoselective monomethylation of primary amines using methanol under mild conditions.
引用
收藏
相关论文
共 177 条
  • [1] Magano J(2011)Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals Chem. Rev. 111 2177-2250
  • [2] Dunetz JR(2010)The mechanism of the modified Ullmann reaction Dalton Trans. 39 10338-10351
  • [3] Sperotto E(2015)Late transition metal-catalyzed hydroamination and hydroamidation Chem. Rev. 115 2596-2697
  • [4] van Klink GPM(2015)Substitution of alcohols by Chem. Soc. Rev. 44 2305-2329
  • [5] van Koten G(2010)-nucleophiles via transition metal-catalyzed dehydrogenation Chem. Rev. 110 681-703
  • [6] de Vries JG(2007)Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis Adv. Synth. Catal. 349 1555-1575
  • [7] Huang L(2011)Borrowing hydrogen in the activation of alcohols ChemCatChem 3 1853-1864
  • [8] Arndt M(2010)The catalytic amination of alcohols Chem. Rev. 110 1611-1641
  • [9] Gooßen K(2013)Hydrogen autotransfer in the Science 341 249-260
  • [10] Heydt H(2015)-alkylation of amines and related compounds using alcohols and amines as electrophiles Org. Process Res. Dev. 19 1400-1410