Heterogeneous catalysis with nickel-on-graphite (Ni/Cg): Reduction of aryl tosylates and mesylates

Angewandte Chemie - International Edition

Volumn 45, Issue 5, 2006, Pages 800-803

  Lipshutz, Bruce H ^a   Frieman, Bryan A ^a   Butler, Tom ^a   Kogan, Vladimir ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aryl tosylates; Graphite; Heterogeneous catalysis; Nickel; Reduction

Indexed keywords

ARYL TOSYLATES; NICKEL-ON-GRAPHITE; TRIFLATE DERIVATIVES;

CATALYSTS; DERIVATIVES; GRAPHITE; NICKEL; REDUCTION;

CATALYSIS;

GRAPHITE; MESYLIC ACID DERIVATIVE; NICKEL; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; OXIDATION REDUCTION REACTION; PARTICLE SIZE; RADIATION EXPOSURE; SYNTHESIS;

CATALYSIS; GRAPHITE; MESYLATES; MICROWAVES; MOLECULAR STRUCTURE; NICKEL; OXIDATION-REDUCTION; PARTICLE SIZE; TOSYL COMPOUNDS;

EID: 31444445995     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502887     Document Type: Article

References (23)

1. W. Ruedorff, Adv. Inorg. Chem. Radiochem. 1959, 1, 223.
2. A. Furstner, F. Hofer, H. Weidmann, Carbon 1991, 29, 915;
3. D. Savoia, C. Trombini, A. Umani-Ronchi, Pure Appl. Chem. 1985, 57, 1887.
4. H. Shioyama, Synth. Met. 2000, 114, 1.
5. For an example that involves the aglycon of vancomycin, see D. A. Evans, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. Am. Chem. Soc. 1993, 115, 6426;
6. D. A. Evans, C. J. Dinsmore, Tetrahedron Lett. 1993, 34, 6029.
7. a) K. Sasaki, T. Kubo, M. Sakai, Y. Kuroda, Chem. Lett. 1997, 617;
8. b) A. J. Barlett, J. S. E. Holker, E. O'Brien, T. J. Simpson, J. Chem. Soc. Perkin Trans. 1 1983, 667;
9. c) W. Cabri, S. De Bernardis, F. Francalanci, S. Penco, J. Org. Chem. 1990, 55, 350.
10. R. C. Larock, Comprehensive Organic Reactions, 2nd ed., Wiley-VCH, New York, 1999.
11. J. Saa, M. Dopico, G. Martorell, A. Garcia-Raso, J. Org. Chem. 1990, 55, 991.
12. 3 appears to have an important influence on the extent of conversion; use of fresh hydride, therefore, is strongly recommended.
13. a) Microwave Assisted Organic Synthesis (Eds.: J. P. Tierney, P. Lidstrom), Blackwell Publishing, 2005 (cf. http://www.blackwell-publishing.com/ book.asp?ref=1405115602andsite=l);
14. b) A. K. Bose, M. S. Manhas, S. N. Ganguly, A. H. Sharma, B. K. Banik, Synthesis 2002, 1578.
15. A Personal Chemistry Emrys Optimizer was used in this study and has recently been replaced by the Biotage Initiator; cf. http://www.biotagedcg.com/ DynPage.aspx?id=4193andmn1=919andmn2=1149.
16. For example, see R. K. Arvela, N. E. Leadbeater, Org. Lett. 2005, 7, 2101;
17. for a review, see: B. Desai, C. O. Kappe in Top. Curr. Chem. (Ed.: A. Kirschning), Springer, 2004, pp. 177-207.
18. A. W. Varnes, Handbook of Instrumental Techniques for Analytical Chemistry (Ed.: F. Settle), Prentice Hall, Upper Saddle River, NJ, 1997, p. 395;
19. Inductively Coupled Plasma Mass Spectrometry (Ed.: A. Montaser), Wiley-VCH, New York, 1998.
20. Although all examples in Table 1 were run with 1 mmol of reactant, the scale was increased to 5 mmol for the case of tosylate 9; under otherwise identical conditions (albeit for 12 vs. 6 h), the reaction led to a 90% yield of isolated product of the reduced material.
21. Data was acquired using a JEOL 2011 STEM operated at 200 keV; the EDX detector is an EDAX Genesis.
22. B. H. Lipshutz, S. Tasler, W. Chrisman, B. Spliethoff, B. Tesche, J. Org. Chem. 2003, 68, 1177.
23. B. H. Lipshutz, B. A. Frieman, H. Birkedal, Org. Lett. 2004, 6, 2305.