Catalytic reductive coupling of epoxides and aldehydes: Epoxide-ring opening precedes carbonyl reduction

Angewandte Chemie - International Edition

Volumn 44, Issue 1, 2004, Pages 129-132

  Molinaro, Carmela ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aldehydes; Coupling reactions; Epoxides; Nickel; Rhodium

Indexed keywords

ACETOPHENONE; ALDEHYDE; BENZOPHENONE; BORON; CARBONYL DERIVATIVE; CYCLOHEXANONE; EPOXIDE; ETHYLENE; FREE RADICAL; ISOBUTYRALDEHYDE; KETONE; NICKEL; OCTANE; OCTANONE; OCTENE 1,2 OXIDE; PHOSPHINE DERIVATIVE; TRIBUTYL PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL OXYGEN DEMAND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; ROOM TEMPERATURE; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RHODIUM;

EID: 11244320357     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461705     Document Type: Article

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25. Nickella(II)oxetanes have not been isolated in pure form but have been proposed as intermediates in catalytic reactions: a) R. J. De Pasquale, J. Chem. Soc. Chem. Commun. 1973, 157-158; b) J.-E. Bäckvall, O. Karlsson, S. O. Ljunggren, Tetrahedron Lett. 1980, 21, 4985-4988; c) A. Miyashita, T. Shimada, A. Sugawara, H. Nohira, Chem. Lett. 1986, 1323-1326; For computational studies, see: d) J.-E. Bäckvall, F. Bökman, M. R. A. Blomberg, J. Am. Chem. Soc. 1992, 114, 534-538; e) M. Mavrikakis, D. J. Doren, M. A. Barteau, J. Phys. Chem. B 1998, 102, 394-399; f) J. W. Medlin, M. Mavrikakis, M. A. Barteau, J. Phys. Chem. B 1999, 103, 11169-11175; g) For gasphase studies (Ni), see: E. Kline, R. H. Hauge, J. L. Margrave, H. Zakya, High Temp. Sci. 1990, 30, 69-82.
26. Nickella(II)oxetanes have not been isolated in pure form but have been proposed as intermediates in catalytic reactions: a) R. J. De Pasquale, J. Chem. Soc. Chem. Commun. 1973, 157-158; b) J.-E. Bäckvall, O. Karlsson, S. O. Ljunggren, Tetrahedron Lett. 1980, 21, 4985-4988; c) A. Miyashita, T. Shimada, A. Sugawara, H. Nohira, Chem. Lett. 1986, 1323-1326; For computational studies, see: d) J.-E. Bäckvall, F. Bökman, M. R. A. Blomberg, J. Am. Chem. Soc. 1992, 114, 534-538; e) M. Mavrikakis, D. J. Doren, M. A. Barteau, J. Phys. Chem. B 1998, 102, 394-399; f) J. W. Medlin, M. Mavrikakis, M. A. Barteau, J. Phys. Chem. B 1999, 103, 11169-11175; g) For gasphase studies (Ni), see: E. Kline, R. H. Hauge, J. L. Margrave, H. Zakya, High Temp. Sci. 1990, 30, 69-82.
27. Nickella(II)oxetanes have not been isolated in pure form but have been proposed as intermediates in catalytic reactions: a) R. J. De Pasquale, J. Chem. Soc. Chem. Commun. 1973, 157-158; b) J.-E. Bäckvall, O. Karlsson, S. O. Ljunggren, Tetrahedron Lett. 1980, 21, 4985-4988; c) A. Miyashita, T. Shimada, A. Sugawara, H. Nohira, Chem. Lett. 1986, 1323-1326; For computational studies, see: d) J.-E. Bäckvall, F. Bökman, M. R. A. Blomberg, J. Am. Chem. Soc. 1992, 114, 534-538; e) M. Mavrikakis, D. J. Doren, M. A. Barteau, J. Phys. Chem. B 1998, 102, 394-399; f) J. W. Medlin, M. Mavrikakis, M. A. Barteau, J. Phys. Chem. B 1999, 103, 11169-11175; g) For gasphase studies (Ni), see: E. Kline, R. H. Hauge, J. L. Margrave, H. Zakya, High Temp. Sci. 1990, 30, 69-82.
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31. II metallaoxetanes: a) R. Schlodder, J. A. Ibers, M. Lenarda, M. Graziani, J. Am. Chem. Soc. 1974, 96, 6893-6900; b) M. Lenarda, R. Ros, O. Traverso, W. D. Pitts, W. H. Baddley, M. Graziani, Inorg. Chem. 1977, 16, 3178-3182; c) K.-T. Aye, L. Gelmini, N. C. Payne, J. J. Vittal, R. J. Puddephatt, J. Am. Chem. Soc. 1990, 112, 2464-2465; d) Nickella(II)azetidine: B. L. Lin, C. R. Clough, G. L. Hillhouse, J. Am. Chem. Soc. 2002, 124, 2890-2891.
32. II metallaoxetanes: a) R. Schlodder, J. A. Ibers, M. Lenarda, M. Graziani, J. Am. Chem. Soc. 1974, 96, 6893-6900; b) M. Lenarda, R. Ros, O. Traverso, W. D. Pitts, W. H. Baddley, M. Graziani, Inorg. Chem. 1977, 16, 3178-3182; c) K.-T. Aye, L. Gelmini, N. C. Payne, J. J. Vittal, R. J. Puddephatt, J. Am. Chem. Soc. 1990, 112, 2464-2465; d) Nickella(II)azetidine: B. L. Lin, C. R. Clough, G. L. Hillhouse, J. Am. Chem. Soc. 2002, 124, 2890-2891.
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40. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
41. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
42. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
43. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
44. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
45. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
46. Water: a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; b) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315; c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638; d) L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362; phenols and aliphatic alcohols: e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688; f) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377; g) carboxylic acids: E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
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55. 3P is included in the reaction, neither product formation nor aldehyde reduction is observed.
56. For acceleration of Rh-catalyzed reactions by bases, see: a) hydrogenation: W. S. Knowles, M. J. Sabacky, B. D. Vineyard, Ann. N. Y. Acad. Sci. 1970, 172, 232-237; b) reductive C-C bond formation: H.-Y. Jang, R. R. Huddleston, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 15156-15157.
57. For acceleration of Rh-catalyzed reactions by bases, see: a) hydrogenation: W. S. Knowles, M. J. Sabacky, B. D. Vineyard, Ann. N. Y. Acad. Sci. 1970, 172, 232-237; b) reductive C-C bond formation: H.-Y. Jang, R. R. Huddleston, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 15156-15157.
58. In the absence of aldehyde, a β-H abstraction by Rh in B would give a boron enolate and, upon workup, a methyl ketone, accounting for the results in Equation (5).
59. "Nuclear Magnetic Resonance Spectroscopy of Boron Compounds Containing Two-, Three-, and Four-Coordinate Boron": B. Wrackmeyer in Annual Reports on NMR Spectroscopy, Vol. 20 (Ed.: G. A. Webb), Academic Press, San Diego, 1988, pp. 61-204.
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