过渡金属催化磷—氢键的转化反应

doi:10.6023/cjoc201207024

摘要/Abstract

有机膦化合物在有机合成、催化、生化、医药以及材料等各个领域都起重要的作用. 主要总结了本课题组近几年来在过渡金属催化磷—氢化合物的转化反应研究方面取得的进展, 包括磷—氢化合物对各种碳—碳不饱和化合物的区域立体选择性加成反应、不对称磷—氢加成反应和磷—氢化合物与碳—氢和杂原子—氢化合物的氧化或脱氢偶联反应. 我们开发的反应提供了一系列制备各类不同精细有机膦化合物的相对高效和高原子经济性的新方法, 相关反应的机理也将做适当讨论.

关键词: 过渡金属催化剂, 磷—氢化合物, 区域立体选择加成反应, 碳—碳不饱和化合物, 氧化/脱氢偶联反应, 碳—氢和杂原子—氢化合物, 精细有机膦化合物

Organophosphorus compounds are of high importance in organic synthesis, catalysis, biochemistry, pharmaceuticals, and material science. In this account, we summarize our recent studies on transition metal-catalyzed transformations of P(O)—H compounds, mainly the regio- and stereo-selective additions of P(O)—H bonds to carbon—carbon unsaturated compounds, asymmetric hydrophosphorylation reactions, and oxidative/dehydrogenative cross-couplings of P(O)—H bonds with C—H and heteroatom—H bonds. These new reactions provided a series of efficient and atom economic, general and green ways for the preparation of a variety of versatile organophosphorus compounds. Mechanistic aspects related to the catalytic processes are also discussed.

Key words: transition metal catalysts, P(O)-H compounds, regio- and stereo-selective addition, carbon-carbon unsaturated compounds, oxidative/dehydrogenative cross-coupling, carbon-H and heteroatom-H compounds, fine organophosphorus compounds

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徐清, 赵长秋, 周永波, 尹双凤, 韩立彪. 过渡金属催化磷—氢键的转化反应[J]. 有机化学, 2012, 32(10): 1761-1775.

Xu Qing, Zhao Changqiu, Zhou Yongbo, Yin Shuangfeng, Han Libiao. Transition Metal-Catalyzed Transformations of P(O)—H Bonds[J]. Chin. J. Org. Chem., 2012, 32(10): 1761-1775.

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参考文献

[1] (a) Quin, L. D. A Guide to Organophosphorus Chemistry, Wiley-Interscience, New York, 2000.

(b) Sasaki, M. In Chirality in Agrochemicals, Eds.: Kurihara, N.; Miyamoto, J., Wiley & Sons, Chichester, 1998, p. 85.

(c) Imamoto, T. In Handbook of Organophosphorus Chemistry, Ed.: Engel, R., Marcel Dekker, New York, 1992, Chapter 1.

(d) Crepy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1.

[2] Arbusov, B. A. Pure Appl. Chem. 1964, 9, 307.

[3] (a) DuBois, D. L.; Myers, W. H.; Meek, D. W. Dalton Trans. 1975, 1011.

(b) Wolfsberger, W. Chem.-Ztg. 1990, 114, 353.

(c) Rauhut, M. M.; Currier, H. A.; Semsel, A. M.; Wystrach, V. P. J. Org. Chem. 1961, 26, 5138.

[4] (a) Rauhut, M. M.; Hechenbleikner, I.; Currier, H. A.; Schaefer, F. C.; Wystrach, V. P. J. Am. Chem. Soc. 1959, 81, 1103.

(b) King, R. B.; Cloyd, J. C. Jr.; Kapoor, P. N. J. Chem. Soc., Perkin Trans. 1 1973, 2226.

(c) Habib, M.; Trujillo, H.; Alexander, C. A.; Storhoff, B. N. Inorg. Chem. 1985, 24, 2344.

[5] (a) Riant, O.; Mostefai, N.; Courmarcel, J. Synthesis 2004, 2943.

(b) Hayashi, T. Catal. Today 2000, 62, 3.

(c) Carroll, A. M.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609.

(d) Vogels, C. M.; Westcott, S. A. Curr. Org. Chem. 2005, 9, 687.

[6] (a) Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218.

(b) Glueck, D. S. Coord. Chem. Rev. 2008, 252, 2171.

(c) Prim, D.; Campagne, J.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.

(d) Beletskaya, I. P.; Kazankova, M. Russ. J. Org. Chem. 2002, 38, 1391.

(e) Engel, R.; Cohen, J. I. Synthesis of Carbon-Phosphorus Bonds, 2nd ed., CRC Press, Boca Raton, 2003.

[7] Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.

[8] Lin, K. US 3673285, 1972 [Chem. Abstr. 1972, 77, 101890].

[9] Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.

[10] Han, L.-B.; Choi, N.; Tanaka, M. Organomettalics 1996, 15, 3259.

[11] (a) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.

(b) Delacroix, O.; Gaumont, A. C. Curr. Org. Chem. 2005, 9, 1851.

(c) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctiona- lization, Eds.: Togni, A.; Grützmacher, H., Wiley-VCH, Weinheim, 2001, pp. 143～170.

(d) Greenberg, S.; Stephan, D. W. Chem. Soc. Rev. 2008, 37, 1482.

(e) Beletskaya, I. P.; Kabachnik, M. M. Mendeleev. Commun. 2008, 18, 113.

(f) Coundray, L.; Montchamp, J.-L. Eur. J. Org. Chem. 2008, 3601.

(g) Beletskaya, I. P.; Moberg, C. Chem. Rev. 2006, 106, 2320.

(h) Xu, Q.; Han, L.-B. J. Organomet. Chem. 2011, 696, 130.

(i) Xu, Q.; Han, L.-B. Sci. Sin. Chim. 2010, 40, 802 (in Chinese).

(徐清，韩立彪，中国科学: 化学 2010, 40, 802.)

[12] Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem., Int. Ed. 2001, 40, 1929.

[13] Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080.

[14] (a) Han, L.-B. 225th National Meeting of the American-Chemical-Society, New Orleans, Louisiana, Abstracts of Papers of the American Chemical Society, 2003, 225, U148.

(b) Han, L.-B. JP 3041396, 2000 [Chem. Abstr. 2000, 133, 120468].

(c) Han, L.-B. JP 3007984, 2000 [Chem. Abstr. 2000, 133, 105157].

[15] Xu, Q.; Shen, R.; Ono, Y.; Nagahata, R.; Shimada, S.; Goto, M.; Han, L.-B. Chem. Commun. 2011, 47, 2333.

[16] Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. 1998, 37, 94.

[17] Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929.

[18] Han, L.-B.; Ono, Y.; Yazawa, Y. Org. Lett. 2005, 7, 2909.

[19] Hirai, T.; Han, L.-B. J. Am. Chem. Soc. 2006, 128, 7422.

[20] Han, L.-B.; Zhao, C.-Q.; Tanaka, M. JP 3877151, 2007 [Chem. Abstr. 2002, 137, 185677].

[21] Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.

[22] Han, L.-B.; Zhao, C.-Q.; Onozawa, S.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.

[23] (a) Xu, Q.; Zhao, C.-Q.; Han, L.-B. J. Am. Chem. Soc. 2008, 130, 12648.

(b) Now these optically pure H-phosphinates can be purchased from Katayama Chemical Industries Co. Ltd. (http://www.kataya- makagaku.co.jp).

[24] Han, L.-B.; Zhao, C.-Q.; Tanaka, M. JP 3777397, 2006 [Chem. Abstr. 2002, 137, 247817].

[25] (a) Han, L.-B.; Zhao, C.-Q. J. Org. Chem. 2005, 70, 10121.

(b) Hirai, T.; Han, L.-B. Org. Lett. 2007, 9, 53.

(c) Wang, G.; Shen, R.; Xu, Q.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 3890.

(d) Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 7924.

[26] (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rew. 1994, 94, 1375.

(b) Korpium, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842.

(c) Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.

(d) Oshiki, T.; Imamoto, T. Bull. Chem. Soc. Jpn. 1990, 63, 3719.

[27] Han, L.-B.; Ono, Y.; Xu, Q.; Shimada, S. Bull. Chem. Soc. Jpn. 2010, 83, 1086.

[28] (a) Nesterov, L. W.; Sabirova, R. A.; Krepisheva, N. E.; Mutalapova, R. I. Dokl. Akad. Nauk SSSR 1963, 148, 1085.

(b) Holmes, R. R. Pentacoordinated Phopshorus, Vols. 1 and 2, ACS, Washington, 1980.

(c) Tebby, J. C. In Phosphorus-Carbon Hererocyclic Chemistry: The Rise of A New Domain, Ed.: Mathey, F., Pergamon, Amsterdam, 2001, Chapter 6.3.

(d) Kawashima, T. In Chemistry of Hypervalent Compounds, Ed.: Akiba, K., Wiley, New York, 1999, Chapter 6.

[29] Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407.

[30] Xu, Q.; Han, L.-B. Org. Lett. 2006, 8, 2099.

[31] (a) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196.

(b) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2000, 42, 297.

[32] (a) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.

(b) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062.

(c) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191.

(d) Klussmann, M.; Sureshkumar, D. Synthesis 2010, 353.

(e) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.

(f) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.

(g) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.

(h) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.

(i) Armstrong, A.; Collins, J. C. Angew. Chem., Int. Ed. 2010, 49, 2282.

(j) Zhao, D.; You, J.; Hu, C. Chem. Eur. J. 2011, 17, 5466.

(k) Shao, Z.; Peng, F. Angew. Chem., Int. Ed. 2010, 49, 9566.

(l) Hirano, K.; Miura, M. Synlett 2011, 294.

(m) Stefani, H. A.; Guarezemini, A. S.; Cella, R. Tetrahedron 2010, 66, 7871.

[33] Han, L.-B.; Ono, Y.; Shimada, S. J. Am. Chem. Soc. 2008, 130, 2752.

[34] Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956.

[35] Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2007, 272.

[36] Han, L.-B.; Tilley, T. D. J. Am. Chem. Soc. 2006, 128, 13698.

[37] Zhou, Y.; Yin, S.; Gao, Y.; Zhao, Y.; Goto, M.; Han, L.-B. Angew. Chem., Int. Ed. 2010, 49, 6852.

[38] (a) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.

(b) Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49～50, 263.

(c) Horner, L.; Lindel, H. Phosphorus, Sulfur Silicon Relat. Elem. 1984, 20, 161.

(d) Pietrusiewicz, K. M.; Wisniewski, W.; Zablocka, M. Tetrahedron 1989, 45, 337.

(e) Collins, D. J.; Rowley, L. E.; Swan, J. M. Aust. J. Chem. 1974, 27, 841.

(f) Polikarpov, Y. M.; Sacherbalkov, B. K.; Medved, T. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 2114.

(g) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991.

(h) Brunner, H.; Limmer, S. J. J. Organomet. Chem. 1991, 417, 173.

(i) Cavalla, D.; Warren, S. Tetrahedron Lett. 1982, 23, 4505.

[39] Han, L.-B.; Huang, Z.; Matsuyama, S.; Ono, Y. Zhao, C.-Q. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5328 and references cited therein. (a) Haynes, R. K.; Vonwiller, S. C.; Hambley, T. W. J. Org. Chem. 1989, 54, 5162.

(b) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785.

(c) Birse, E. F.; Ironside, M. D.; Murray, A. W. Tetrahedron Lett. 1995, 36, 6309.

(d) Yamashita, K.; Oshikawa, T.; Imoto, H. JP 62207281, 1987 [Chem. Abstr. 1988, 108, 167691m].

(e) Yamashita, K.; Imoto, H.; Tamada, Y.; Oshikawa, T. JP 01045390, 1989 [Chem. Abstr. 1989, 111, 115592x］