IRON-CATALYZED ARYL SELECTIVE ACYLATION OF MIXED DIORGANOZINCS

Abstract

Iron-catalyzed acylation of mixed alkylarylzincs with aromatic acyl halides in THF provides a new route for aryl-aroyl coupling. This procedure is an atom-economic supplement to transition metal-catalyzed acylation of diorganozincs.

Keywords

• Mixed diorganozincs,acylation,iron catalyst

References

1. R. K. Dieter, Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis. Tetrahedron, 55/14 (1999) 4177-4236.
2. P. Knochel and G. A. Molander (Eds.), Comprehensive Organic Synthesis, 2nd. Edition, Page 9, line 12, Vol.3, Elsevier, 2014.
3. R. C. Larock, (Ed.), Comprehensive Organic Transformations, 2nd Edition, Chapter 9, Wiley-VCH, 201 0.
4. B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, London, 1995.
5. G. S. Silvermann and P. E. Rakita, (Eds.), Handbook of Grignard Reagents, Marcel Dekker, New York, 1996.
6. C. Malanga, L. A. Aronica and L. Lardicci, Direct Ni mediated synthesis of ketones from acyl bromides and Grignard reagents. Tetrahedron Letters 36/50 (1995) 9185-9188.
7. H. Maeda, I. Okamoto and H. Ohmari, Reactions of in situ formed acyl tributylphosphonium ions with Grignard reagents as an effective route to ketones from acid chlorides. Tetrahedron Letters 37/30 (1996) 5381-5384.
8. M. M. Dell’ Anna, P. Mastrorilli, C. F. Nobile, G. Marchese and M. R. Taurino, Coupling reactions between acyl chlorides and Grignard reagents in the presence of a supported Fe(III)-complex. Journal of Molecular Catalysis A: Chemical161/1-2 (2000) 239-243.

9. B. Scheiper, M. Bonnekessel, H. Krause and A. Fürstner, Selective Iron-catalyzed Cross-Coupling Reactions of Grignard reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes. Journal of Organic Chemistry 69/11 (2004) 3943-3949 and references cited therein.
10. C. Duplais, F. Bures, I. Sapountzis, T.j. Korn, G. Cahiez and P. Knochel, An efficient synthesis of diaryl ketones by iron-catalyzed arylation of aroyl cyanides. Angewandte Chemie International Edition in English 43/22 (2004) 2968-2970.
11. X. Wang, L. Zhang, X. Sung, Y. Xu, D. Krishnamurthy and C. H. Scnanayake, Addition of Grignard reagents to aryl acid chlorides: An efficient synthesis of aryl ketones. Organic Letters. 7 (2005) 5593-5595.
12. B. D. Sherry and A. Fürstner, The promise and challenge of Iron-catalyzed Cross-Coupling. Accounts of Chemical Research 41/11 (2008) 1500-1511.
13. M. S. Growda, S. S. Pande, R. A. Ramakrishrra and K. R. Prabhu, Acylation of Grignard reagents mediated by N-methylpyrrolidone: A remarkable selectivity for the synthesis of ketone. Organic and Biomolecular Chemistry 9 (2011) 5365-5368.
14. J. Nakatoni and T. Nozoe, Preparation of trifluoromethylphenyl magnesium halides in the presence of LiCl and synthesis of 2′-trifluoromethyl-aromatic ketones. Organic Process Research & Development20/9 (2016) 1633-1636.
15. N. Krause, (Ed.), Modern Organocopper Chemistry, Wiley-VCH, Weinheim, 2001.
16. Z. Rappoport and I. Marek, (Eds.), Patai’s The Chemistry of Organocopper Compounds, Wiley, Chichester, 2009.
17. Z. Rappoport, Patai’s The Chemistry of Organozinc Compounds, (Ed. I. Marek) Wiley-VCH, Chichester, 2007.
18. E. Erdik, Organozinc Reagents in Organic Synthesis, CRC Press, New York, 1996.
19. H. S. Jung and S. H. Kim, Direct preparation of new organozinc reagents, aminophenylzinc iodides, and their applications. Tetrahedron Letters 56/8 (2015) 1004-1006.
20. D. Wang and Z. Zhang, Palladium-catalyzed cross-coupling reactions of carboxylic anhydrides with organozinc reagents. Organic Letters 5/24 (2003) 4645-4648.
21. H. Xu, K. E-Kovi and C. Wolf, Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents. Journal of Organic Chemistry 73/19 (2008) 7638-7650.
22. A. H. Cherney and S .E. Reisman, Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones. Tetrahedron 70 (2014) 3559-3565.
23. C. K. Reddy and P. Knochel, New cobalt‐ and iron‐catalyzed reactions of organozinc compounds. Angewandte Chemie International Edition in English 35/15 (1996) 1700-1701.
24. H. Fillon, C. Gosmini and J. Perichon, A convenient method for the preparation of aromatic ketones from acyl chlorides and arylzinc bromides using a cobalt catalysis. Tetrahedron, 59/41 (2003) 8199-8202.
25. I. Kazmierski, M. Bastienne, C. Gosmini, J. M. Paris and J. Perichon, Convenient processes for the synthesis of aromatic ketones from aryl bromides and carboxylic anhydrides using a cobalt catalysis. Journal of Organic Chemistry 69/3 (2004) 936-942.
26. A. D. Benische, M. Leroux, I. Knoll and P. Knochel, Iron-catalyzed acylation of polyfunctionalized aryl- and benzylzinc halides with acid chlorides. Organic Letters18/15 (2016) 3626-3629.
27. Y. Zhang and T. Rovis, A Unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters. Journal of American Chemical Society 126/49 (2004) 15964-15965.
28. S. H. Kim and R. D. Rieke, Preparation of aryl ketones via Ni-catalyzed Negishi-coupling reactions with acid chlorides. Tetrahedron Letters 52/13 (2011) 1523-1526.
29. H. H. Cho and S. -H. Kim, A Versatile protocol for the preparation of highly hindered aryl ketones using organozinc reagents. Bulletin of the Korean Chemical Society 33/9 (2012) 3083-3086.
30. H. Yin, C. Zhao, H. You, K. Lin and H. Gong, Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides. Chemical Communication 48 (2012) 7034-7036.
31. S. Niwa and K. J. Soai, Catalytic asymmetric synthesis of optically active alkynyl alcohols by enantioselective alkynylation of aldehydes and by enantioselective alkylation of alkynyl aldehydes. Journal of the Chemical Society, Perkin Transactions 14 (1990) 937-943.
32. W. Oppolzer and R. N. Radinov, Synthesis of (R)-(-)-muscone by an asymmetrically catalyzed macrocyclization of an omega-alkynal. Journal of American Chemical Society 115/4 (1993) 1593-1594.
33. E. Laloe and W. Srebnik, A study of methyl and tert-butyl as non-migrating groups in the reaction of Me(organyl)zinc and t-Bu(organyl)zinc with aldehydes. Tetrahedron Letters 35/31 (1994) 5587-5590.
34. S. Berger, F. Langer, C. Lutz, P. Knochel, T. A. Mobley and C. K. Reddy, β‐Silly diorganozinc compounds-A New class of useful zinc reagents. Angewandte Chemie International Edition in English 36 (1997) 1496-1498
35. C. Lutz and P. Knochel, Highly enantioselective addition of mixed diorganozincs to aldehydes. Journal of Organic Chemistry 62/22 (1997) 7895-7898.
36. P. Jones and P. Knochel, Conjugate Michael-additions with mixed diorganozincs. Journal of the Chemical Society, Perkin Transactions 121 (1997) 3117-3118.
37. P. Jones, C. K. Reddy and P. Knochel, Conjugate Michael additions with mixed diorganozincs. Tetrahedron 54/8 (1998) 1471-1490.
38. P. Wipf and S. Ribe, Zirconocene-Zinc, Transmetalation and in situ catalytic asymmetric addition to aldehydes. Journal of Organic Chemistry 63/19 (1998) 6454-6455.
39. B. H. Lipshutz and W. V. Randall, Cu(I)-catalyzed substitution reactions of activated vinyl triflates with functionalized organozinc reagents. Tetrahedron Letters 40/15 (1999) 2871-2874.
40. C. Lutz, P. Jones and P. Knochel, Neopentyl and neophyl groups: New nontransferable groups for organocopper and organozinc chemistry. Synthesis 2 (1999) 312-316.
41. C. Bolm, N. Herman, J. P. Hildebrand and K. Muniz, Asymmetric, catalytic phenyl transfer to aldehydes: Enantioselective synthesis of diarylmethanols. Angewandte Chemie International Edition in English 39/19 (2000) 3465-3467.
42. E. Hupe and P. Knochel, Stereoselective synthesis of secondary organozinc reagents and their reaction with heteroatomic electrophiles. Organic Letters 3/1 (2001) 127-130.
43. A. Rimkus and N. Sewald, Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins. Organic Letters 4/19 (2002) 3289-3291.
44. A. E. Jensen and P. Knochel, Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides. Journal of Organic Chemistry 67/1 (2002) 79-85.
45. E. Hupe, M. I. Calaza and P. Knochel, Synthesis and reaction of secondary and primary diorganozinc reagents using a boron–zinc exchange reaction: A useful method for the stereo- and regioselective formation of new carbon-carbon bonds. Journal of Organometallic Chemistry 680/1-2 (2003) 136-142.
46. J. F. Trawerse, A. H. Hoveyda and M. Snapper, Enantioselective synthesis of propargylamines through Zr-catalyzed addition of mixed alkynylzinc reagents to arylimines. Organic Letters 5/18 (2003) 3273-3275.
47. D. Soorukram and P. Knochel, Enantioselective synthesis of α-Ionone derivatives using an anti SN2‘ substitution of functionalized zinc organometallics. Organic Letters 6/14 (2004) 2409-2411.
48. M. Fontes, X. Verdaguer, L. Sola, M. A. Pericas and A. Riera, 2-Piperidino-1,1,2-triphenylethanol: a highly effective catalyst for the enantioselective arylation of aldehydes. Journal of Organic Chemistry 69/7 (2004) 2532-2543.
49. J. Rudolph, C. Bolm and P. O. Norby, New insights into the stereoselectivity of the aryl zinc addition to aldehydes. Journal of American Chemical Society 127/5 (2005) 1548-1552.
50. J. G. Kim and P. H. Walsh, From aryl bromides to enantioenriched benzylic alcohols in a single flask: Catalytic asymmetric arylation of aldehydes. Angewandte Chemie International Edition in English 45 (2006) 4175-4178.
51. J. B. Johnson, P. Yu, P. Fink, E. A. Bercot and T. Rovis, Selective substituent transfer from mixed zinc reagents in Ni-catalyzed anhydride alkylation. Organic Letters 8/19 (2006) 4307-4310.
52. E. Erdik and Ö. Ö. Pekel, Reactivities of mixed organozinc and mixed organocopper reagents: 1. Solvent controlled organic group transfer from mixed diorganozincs. Journal of Organometallic Chemistry 693/2 (2008) 338-342.
53. E. Erdik and Ö. Ö. Pekel, Reactivities of mixed organozinc and mixed organocopper reagents, 2. Selective n-alkyl transfer in tri-n-butylphosphine-catalyzed acylation of n-alkyl phenylzincs; an atom economic synthesis of n-alkyl aryl ketones. Tetrahedron Letters 50/13 (2009) 1501-1503.
54. E. Erdik, F. Eroglu, M. Kalkan, Ö. Ö. Pekel, D. Özkan and E. Z. Serdar, Reactivities of mixed organozinc and mixed organocopper reagents: 9. Solvent dependence of group transfer selectivity in sp3C coupling and acylation of mixed diorganocuprates and diorganozincs. Journal of Organometallic Chemistry 745-746 (2013) 235-241.
55. Ö. Ö. Pekel and E. Erdik, Reactivity of mixed organozinc and mixed organocopper reagents: 10 Comparison of the transferability of the same group in acylation of mixed and homo halozinc diorganocuprates with benzoyl chloride. A kinetic study. Journal of Organometallic Chemistry 751 (2014) 644-653.
56. Ö. Ö. Pekel, Reactivities of mixed organozinc and mixed organocopper reagents. Part 13: Kinetic study for phosphine‐catalyzed acylation of alkylarylzincs and effect of residual group on the transfer rate of alkyl group. Journal of Physical Organic Chemistry 29 (2016) 190-195.
57. Ö. Ö. Pekel, E. Erdik and M. Kalkan, Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs. Turkish Journal of Chemistry 42/3 (2018) 759-767.
58. J. Leonard, B. Lygo and G. Procter, Advanced Practical Organic Chemistry, Blackie, London, 1995.