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Synthesis 2017; 49(17): 3957-3961
DOI: 10.1055/s-0036-1589064
DOI: 10.1055/s-0036-1589064
special topic
A Simple Cobalt(II) Chloride Catalyzed N-Alkylation of Amines with Alcohols
Autoren
Weitere Informationen
Publikationsverlauf
Received: 12. April 2017
Accepted after revision: 30. Mai 2017
Publikationsdatum:
11. Juli 2017 (online)
Dedicated to Professor David Milstein on the occasion of his 70th birthday
Published as part of the Special Topic Cobalt in Organic Synthesis
Abstract
A facile cobalt-catalyzed N-alkylation of amines with alcohols using inexpensive, commercially available CoCl2·6H2O is reported. Employing this readily available cobalt catalyst, a variety of amines with wide functional group tolerance were selectively alkylated under benign conditions.
Key words
cobalt catalysis - N-alkylation - amines - alcohols - hydrogen autotransfer - dehydrogenationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589064.
- Supporting Information (PDF) (opens in new window)
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References
- 1a Pesticide Chemistry and Bioscience . Brooks GT. Roberts TR. Royal Society of Chemistry; Cambridge: 1999
- 1b Pharmaceuticals: Classes, Therapeutic Agents, Areas of Application. Vol. 1-4. McGuire JL. Wiley-VCH; Weinheim: 2000
- 1c Lawrence SA. Amines: Synthesis, Properties and Applications . Cambridge University Press; Cambridge: 2004
- 1d Brown BR. The Organic Chemistry of Aliphatic Nitrogen Compounds . Cambridge University Press; Cambridge: 2004
- 2a Bahn S. Imm S. Neubert L. Zhang M. Nuemann H. Beller M. ChemCatChem 2011; 3: 1853
- 2b Barta K. Ford PC. Acc. Chem. Res. 2014; 47: 1503
- 2c Nandakumar A. Midya SP. Landge VG. Balaraman E. Angew. Chem. Int. Ed. 2015; 54: 11022
- 3a Hamid MH. S. A. Slatford PA. Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
- 3b Nixon TD. Whittlesey MK. Williams JM. J. Dalton Trans. 2009; 753
- 3c Shimizu K.-i. Catal. Sci. Technol. 2015; 5: 1412
- 4a Hollmann D. Tillack A. Michalik D. Jackstell R. Beller M. Chem. Asian J. 2007; 2: 403
- 4b Hamid MH. S. A. Williams JM. J. Chem. Commun. 2007; 725
- 4c Hamid MH. S. A. Williams JM. J. Tetrahedron Lett. 2007; 48: 8263
- 4d Gunanathan C. Milstein D. Angew. Chem. Int. Ed. 2008; 47: 8661
- 4e Hamid MH. S. A. Allen CL. Lamb GW. Maxwell AC. H. Maytum C. Watson AJ. A. Williams JM. J. J. Am. Chem. Soc. 2009; 131: 1766
- 4f Imm S. Bähn S. Neubert L. Neumann H. Beller M. Angew. Chem. Int. Ed. 2010; 49: 8126
- 4g Zhang M. Imm S. Bähn S. Neumann H. Beller M. Angew. Chem. Int. Ed. 2011; 50: 11197
- 4h Fernandez FE. Puerta MC. Valerga P. Organometallics 2012; 31: 6868
- 4i Celaje JJ. A. Zhang X. Zhang F. Kam L. Herron JR. ACS Catal. 2017; 7: 1136
- 5a Morton D. Cole-Hamilton DJ. J. Chem. Soc., Chem. Commun. 1987; 248
- 5b Zweifel T. Naubron J.-V. Grützmacher H. Angew. Chem. Int. Ed. 2009; 48: 559
- 6a Balcells D. Nova A. Clot E. Gnanamgari D. Crabtree RH. Eisenstein O. Organometallics 2008; 27: 2529
- 6b Blank B. Madalska M. Kempe R. Adv. Synth. Catal. 2008; 350: 749
- 6c Prades A. Corberan R. Poyatos M. Peris E. Chem. Eur. J. 2008; 14: 11474
- 6d Gnanamgari D. Sauer EL. O. Schley ND. Butler C. Incarvito CD. Crabtree RH. Organometallics 2009; 28: 321
- 6e Blank B. Michlik S. Kempe R. Adv. Synth. Catal. 2009; 351: 2903
- 6f Kawahara R. Fujita K. Yamaguchi R. J. Am. Chem. Soc. 2010; 132: 15108
- 6g Michlik S. Kempe R. Chem. Eur. J. 2010; 16: 13193
- 6h Saidi O. Blacker AJ. Farah MM. Marsden SP. Williams JM. J. Chem. Commun. 2010; 46: 1541
- 6i Kawahara R. Fujita K. Yamaguchi R. Adv. Synth. Catal. 2011; 353: 1161
- 6j Cumpstey I. Agrawal S. Borbas EK. Martin-Matute B. Chem. Commun. 2011; 47: 7827
- 6k Michlik S. Hille T. Kempe R. Adv. Synth. Catal. 2012; 354: 847
- 6l Agrawal S. Lenormand M. Martin-Matute B. Org. Lett. 2012; 14: 1456
- 6m Li J.-Q. Andersson PG. Chem. Commun. 2013; 49: 6131
- 7a Pan S. Liu J. Li H. Wang Z. Guo X. Li Z. Org. Lett. 2010; 12: 9
- 7b Cui X. Shi F. Zhang Y. Deng Y. Tetrahedron Lett. 2010; 51: 2048
- 7c Zhao Y. Foo SW. Saito S. Angew. Chem. Int. Ed. 2011; 50: 3006
- 7d Bala M. Verma PK. Sharma U. Kumar N. Singh B. Green Chem. 2013; 15: 1687
- 7e Yan T. Feringa BL. Barta K. Nat. Commun. 2014; 5: 5602
- 7f Mastalir M. Stöger B. Pittenauer E. Puchberger M. Allmaier G. Kirchner K. Adv. Synth. Catal. 2016; 358: 3824
- 7g Balaraman E. Nandakumar A. Jaiswal G. Sahoo MK. Catal. Sci. Technol. 2017;
- 8a Rösler S. Ertl M. Irrgang T. Kempe R. Angew. Chem. Int. Ed. 2015; 54: 15046
- 8b Zhang G. Yin Z. Zheng S. Org. Lett. 2016; 18: 300
- 8c Yin Z. Zeng H. Wu J. Zheng S. Zhang G. ACS Catal. 2016; 6: 6546
- 8d Mastalir M. Tomsu G. Pittenauer E. Allmaier G. Kirchner K. Org. Lett. 2016; 18: 3462
- 8e Quintard A. Rodriguez J. ChemSusChem 2016; 9: 28
- 9a Alonso F. Riente P. Yus M. Acc. Chem. Res. 2011; 44: 379
- 9b Martínez-Asencio A. Ramon DJ. Yus M. Tetrahedron 2011; 67: 3140
- 9c Yu X. Liu C. Jiang L. Xu Q. Org. Lett. 2011; 13: 23
- 9d Elangovan S. Neumann J. Sortais J.-B. Junge K. Darcel C. Beller M. Nat. Commun. 2016; 7: 12641
- 9e Bruneau-Voisine A. Wang D. Dorcet V. Roisnel R. Darcel C. Sortais J.-B. J. Catal. 2017; 347: 57
- 9f Neumann J. Elangovan S. Spannenberg A. Junge K. Beller M. Chem. Eur. J. 2017; 23: 5410
- 10 Corre Y. Iali W. Hamdaoui M. Trivelli X. Djukic J.-P. Agbossou-Niedercorn F. Michon C. Catal. Sci. Technol. 2015; 5: 1452