Synthesis and Reactivity of Group 10 Transition Metal Complexes with Alkenylphosphoryl Compounds

doi:10.6023/cjoc201905001

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2183-2187.DOI: 10.6023/cjoc201905001 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

烯基膦氧配位的第10族过渡金属配位化合物的合成和性质

陈铁桥^a, 刘龙^a, 黄添增^a, 韩立彪^b

a 海南大学化学工程与技术学院热带岛屿资源先进材料教育部重点实验室海口 570228;
b 日本产业技术综合研究所筑波 305-8565 日本

收稿日期:2019-05-01 修回日期:2019-06-19 发布日期:2019-07-09
通讯作者: 韩立彪 E-mail:libiao-han@aist.go.jp
基金资助:
国家自然科学基金（No.21871070）和海南省自然科学基金（No.219MS005）资助项目.

Synthesis and Reactivity of Group 10 Transition Metal Complexes with Alkenylphosphoryl Compounds

Chen Tieqiao^a, Liu Long^a, Huang Tianzeng^a, Han Li-Biao^b

a Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, College of Chemical Engineering and Technology, Hainan University, Haikou, Hainan 570228, China;
b National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan

Received:2019-05-01 Revised:2019-06-19 Published:2019-07-09
Contact: 10.6023/cjoc201905001 E-mail:libiao-han@aist.go.jp
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21871070), and the Natural Science Foundation of Hainan Province (No. 219MS005).

1. Synthesis and Reactivity of Group 10 Transition Metal Complexes with Alkenylphosphoryl Compounds.PDF(563KB)

Abstract

Alkenylphosphoryl compounds could quickly replace two phosphine ligands in Pd(PEt₃)₄ at room temperature to produce the corresponding palladium complexes 3a~3e in high yields. Similar nickel and platinium complexes 3f and 3g were also synthesized by the reaction. Complex 3e could react with HOAc to release alkenylphosphoryl compounds gradually. By further addition of 2 equiv. of PEt₃, the reaction could take place completely, generating a phosphoniun 4 as a precipitation. Being similar to Pd(PEt₃)₄, 3d could also undergo hydropalladation with the combination of phenylacetylene and (EtO)₂P(O)H, forming the expected vinyl-Pd-phosphoryl complex, but with a slower reaction rate. The result indicated that alkenylphosphoryl compounds generated from the palladium-catalyzed hydrophosphorylation of alkynes with H-phosphonates might play a negative role in the hydropalladation step of the catalytic cycle. Complexes 3a~3g and phosphonium 4 were charaterized by NMR analysis. The structures of 3a and 4 were also confirmed by X-ray technology.

Key words: alkenylphosphoryl compounds, group 10 transition metals, coordination compounds

Cite this article

Chen Tieqiao, Liu Long, Huang Tianzeng, Han Li-Biao. Synthesis and Reactivity of Group 10 Transition Metal Complexes with Alkenylphosphoryl Compounds[J]. Chin. J. Org. Chem., 2019, 39(8): 2183-2187.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For selected book and reviews, see:(a) Lawrance, G. A. Introduction to Coordination Chemistry, Wiley, Chichester, UK, 2010.
(b) Burgess, J.; Steel, P. J. Coord. Chem. Rev. 2011, 255, 2094.
(c) Steobenau, E. J.; Jordan, R. F. J. Am. Chem. Soc. 2006, 128, 8162.
(d) Harvey, B. G.; Ernst, R. D. Eur. J. Inorg. Chem. 2017, 2017, 1205.
(e) Defieber, C.; Grutzmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482.
(f) Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840.
(g) Feng, X.; Du, H. Chin. J. Org. Chem. 2015, 35, 259(in Chinese). (冯向青,杜海峰,有机化学, 2015, 35, 259.)
[2] For selected reviews, see:(a) Dembitsky, V. M.; Quntar, A. A. A. A.; Haj-Yehia, A.; Srebnik, M. Mini-Rev. Org. Chem. 2005, 2, 91.
(b) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
(c) Wang, H.-Q.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23, 321(in Chinese). (王宏青,刘钊杰,有机化学, 2003, 23, 321.)
[3] (a) Al-Quntar, A. A.-A.; Baum, O.; Reich, R.; Srebnik, M. Arch. Pharm. 2004, 337, 76.
(b) Liu, Z.; MacRitchie, N.; Pyne, S.; Pyne, N. J.; Bittman, R. Bioorg. Med. Chem. 2013, 21, 2503.
(c) Harnden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. J. Med. Chem. 1993, 36, 1343.
(d) Tonelli, F.; Lim, K. G.; Loveridge, C.; Long, J.; Pitson, S. M.; Tigyi, G.; Bittman, R.; Pyne, S.; Pyne, N. J. Cell. Signalling 2010, 22, 1536.
[4] (a) Kosolapoff, G. M. J. Am. Chem. Soc. 1948, 70, 1971.
(b) Mulla, K.; Aleshire, K. L.; Forster, P. M.; Kang, J. Y. J. Org. Chem. 2016, 81, 77 and references cited therein.
[5] Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
[6] (a) Coudray, L.; Montchamp, J.-L. Eur. J. Org. Chem. 2008, 3601.
(b) Delacroix, O.; Gaumont, A. C. Curr. Org. Chem. 2005, 9, 1851.
(c) Xu, Q.; Han, L.-B. J. Organomet. Chem. 2011, 696, 130.
[7] http://www.katayamakagaku.co.jp/products/chemicalproducts/flameretardant/index.html
[8] Chen, T.; Zhao, C.-Q.; Han, L.-B. J. Am. Chem. Soc. 2018, 140, 3139.
[9] (a) Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 8696.
(b) Okuma, K.; Izaki, T. Bull. Chem. Soc. Jpn. 2005, 78, 1831.
(c) Kentaro, O., Koichiro, Y.; Toshiharu, I.; Keiko, Y.; Kosei, S. Bull. Chem. Soc. Jpn. 2007, 80, 1785.
(d) Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2006, 128, 50.
(e) Arisawa, M.; Yamaguchi, M. In ACS Symposium Series, Ed.:Laali, K. K., American Chemical Society, Washington, DC, 2007, Vol. 965, Chapter 22, pp. 477~492.
[10] For a review, see:Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049.
[11] Both electronic and steric factors affect the regioselectivity of hydropalladation, for details, please see Ref.
[8] . A related work on the basis of DFT calculation was also reported, see:Zhang, H.; Bao, X. RSC Adv. 2015, 5, 84636.

烯基膦氧配位的第10族过渡金属配位化合物的合成和性质

Synthesis and Reactivity of Group 10 Transition Metal Complexes with Alkenylphosphoryl Compounds

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments