NiCl2·6H2O/NaBH4 in methanol: A mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Tetrahedron Letters

Volumn 54, Issue 34, 2013, Pages 4540-4543

  Chouhan, Mangilal ^a   Kumar, Kapil ^a   Sharma, Ratnesh ^a   Grover, Vikas ^a   Nair, Vipin A ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Chemoselectivity; Deallylation; Debenzylation; Nickel chloride hexahydrate; Sodium borohydride

Indexed keywords

BORON; ETHER DERIVATIVE; METHANOL; NICKEL; NICKEL CHLORIDE HEXAHYDRATE; REAGENT; SODIUM BOROHYDRIDE; SOLVENT; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION KINETICS; DEBENZYLATION; DEPROTECTION REACTION; REACTION TIME;

EID: 84880279941     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.072     Document Type: Article

References (37)

1. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1991 John Wiley & Sons New York
2. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry Part B: Reactions and Synthesis 5th ed. 2007 Springer Science and Business Media, LLC
3. M.V. Bhatt, and S.U. Kulkarni Synthesis 1983 249
4. B.C. Ranu, and S. Bhar Org. Prep. Proced. Int. 28 1996 371
5. S.A. Weissman, and D. Zewge Tetrahedron 61 2005 7833
6. F.L. Benton, and T.E. Dillon J. Am. Chem. Soc. 64 1942 1128
7. G.I. Feutrill, and R.N. Mirrington Tetrahedron Lett. 11 1970 1327
8. M.E. Jung, and M.A. Lyster J. Org. Chem. 42 1977 3761
9. P.R. Brooks, M.C. Wirtz, M.G. Vetelino, D.M. Rescek, G.F. Woodworth, B.P. Morgan, and J.W. Coe J. Org. Chem. 64 1999 9719
10. H.C. Beyerman, and G.J. Heiszwolf J. Chem. Soc. 1963 755
11. B. Ganem, and V.R. Small Jr. J. Org. Chem. 39 1974 3728
12. J.S. Yadav, S. Chandrasekhar, G. Sumithra, and R. Kache Tetrahedron Lett. 37 1996 6603
13. R.M. Thomas, G.H. Mohan, and D.S. Iyengar Tetrahedron Lett. 38 1997 4721
14. A. Kamal, E. Laxman, and N.V. Rao Tetrahedron Lett. 40 1999 371
15. R.M. Thomas, G.S. Reddy, and D.S. Iyengar Tetrahedron Lett. 40 1999 7293
16. R. Boss, and R. Scheffold Angew. Chem., Int. Ed. Engl. 15 1976 558
17. H.B. Mereyala, and S. Guntha Tetrahedron Lett. 34 1993 6929
18. T. Taniguchi, and K. Ogasawara Angew. Chem., Int. Ed. 37 1998 1136
19. W.H. Hartung, and R. Simonoff Org. React. 7 1953 263
20. P.K. Mandal, and J.S. McMurray J. Org. Chem. 72 2007 6599
21. A. Pastore, S. Valerio, M. Adinolfi, and A. Iadonisi Chem. Eur. J. 17 2011 5881
22. M. Adinolfi, G. Barone, L. Guariniello, and A. Iadonisi Tetrahedron Lett. 40 1999 8439
23. E.J. Reist, V.J. Bartuska, and L. Goodman J. Org. Chem. 29 1964 3725
24. M.H. Park, R. Takeda, and K. Nakanishi Tetrahedron Lett. 28 1987 3823
25. A.G. Sergeev, and J.F. Hartwig Science 332 2011 439
26. M. Tobisu, K. Yamakawa, T. Shimasaki, and N. Chatani Chem. Commun. 2011 2946
27. P. Kelley, S. Lin, G. Edouard, M.W. Day, and T. Agapie J. Am. Chem. Soc. 134 2012 5480
28. A.G. Sergeev, J.D. Webb, and J.F. Hartwig J. Am. Chem. Soc. 134 2012 20226
29. J. Cornella, E. Gómez-Bengoa, and R. Martin J. Am. Chem. Soc. 135 2013 1997
30. V. Kumar, P. Raghavaiah, S.M. Mobin, and V.A. Nair Org. Biomol. Chem. 8 2010 4960
31. V. Kumar, and V.A. Nair Tetrahedron Lett. 51 2010 966
32. G.L. Khatik, R. Khurana, V. Kumar, and V.A. Nair Synthesis 2011 3123
33. V. Kumar, G.L. Khatik, and V.A. Nair Synlett 2011 2997
34. V. Kumar, A. Pal, G.L. Khatik, and V. Nair A Tetrahedron: Asymmetry 23 2012 434
35. G.L. Khatik, V. Kumar, and V.A. Nair Org. Lett. 14 2012 2442
36. M. Chouhan, R. Sharma, and V.A. Nair Org. Lett. 14 2012 5672
37. V. Kumar, K. Kumar, A. Pal, G.L. Khatik, and V.A. Nair Tetrahedron 69 2013 1747