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Alkenylcarbyne Complexes Derived from the Reactions of OsXCl-(PPh3)3(X=H,Cl) with Propargyl Chloride and Phosphine Ligand-Controlled Transformation of Hydride-Carbyne to Carbene
Received date: 2016-08-18
Revised date: 2016-09-04
Online published: 2016-09-06
Supported by
Project supported by the National Basic Research Program of China(973 Program, No. 2012CB821600) and the National Natural Science Foundation of China(No. 21072161).
Reactions of the simple osmium precursors OsHCl(PPh3)3(1) or OsCl2(PPh3)3(2) with 3-chloro-3-methylbut-1-yne afforded OsHCl2(≡CCH=CMe2)(PPh3)2(3) or OsCl3(≡CCH=CMe2)(PPh3)2(4),respectively.Treatment of 3 with Ph2PC≡CPh led to the formation of the tris-diphenyl(phenylethynyl) phosphine alkenylcarbene complex OsCl2(=CHCH=CMe2)(Ph2PC≡CPh)3(5),while complex 4 underwent simple phosphine ligand substitution with Ph2PC≡CPh to give OsCl3(≡CCH=CMe2)(Ph2PC≡CPh)2(6).Presumably,upon the phosphine ligand substitution of PPh3 in 3 by Ph2PC≡CPh,the relatively electron-poor nature of the later decreased the electron density of the osmium center,and thus promoted the transformation of the hydride-carbyne to carbene via the 1,2-shift of the hydride ligand from Os to the carbyne carbon,which was then further facilitated by the coordination of a third less bulky Ph2PC≡CPh ligand to the osmium center to give the stable 18e product 5.
Key words： osmium; carbyne; carbene; diphenyl(phenylethynyl) phosphine; propargyl chloride
Yang Yu , Cai Tao , Wen Tingbin . Alkenylcarbyne Complexes Derived from the Reactions of OsXCl-(PPh3)3(X=H,Cl) with Propargyl Chloride and Phosphine Ligand-Controlled Transformation of Hydride-Carbyne to Carbene[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 176 -184 . DOI: 10.6023/cjoc201608013
[1] For selected general reviews on the chemistry of transition metal carbyne complexes see:
(a) Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schrock, R. R.; Schubert, U.; Weiss, K. In Carbyne Complexes, VCH, Weinheim, Germany, 1988.
(b) Maya, A.; Hoffmeister, H. Adv. Organomet. Chem. 1991, 32, 227.
(c) Engel, P. F.; Pfeffer, M. Chem. Rev. 1995, 95, 2281.
(d) Schrock, R. R. J. Chem. Soc., Dalton Trans. 2001, 2541.
(e) Schrock, R. R. Chem. Rev. 2002, 102, 145.
(f) Shi, C.; Jia, G. Coord. Chem. Rev. 2013, 257, 666.
(g) Herndon, J. W. Coord. Chem. Rev. 2016, 317, 1.
[2] For selective reviews on alkyne metathesis see:
(a) Fürstner, A. Angew. Chem., Int. Ed. 2013, 52, 2794 and references cited therein.
(b) Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748.
(c) Zhang, W.; Moore, J. S. Adv. Synth. Catal. 2007, 349, 93.
(d) Fürstner, A.; Davies, P. W. Chem. Commun. 2005, 2307.
(e) Bunz, H. F. Acc. Chem. Res. 2001, 34, 998.
[3] Selected recent examples of alkyne metathesis:
(a) on Kugelgen, S.; Bellone, D. E.; Cloke, R. R.; Perkins, W. S.; Fischer, F. R. J. Am. Chem. Soc. 2016, 138, 6234.
(b) Wang, Q.; Yu, C.; Long, H.; Du, Y.; Jin, Y.; Zhang, W. Angew. Chem., Int. Ed. 2015, 54, 7550.
(c) Ralston, K. J.; Ramstadius, H. C.; Brewster, R. C.; Niblock, H. S.; Hulme, A. N. Angew. Chem., Int. Ed. 2015, 54, 7086.
(d) Haberlag, B.; Freytag, M.; Jones, P. G.; Tamm, M. Adv. Synth. Catal. 2014, 356, 1255.
(e) Lhermet, R.; Fürstner, A. Chem. Eur. J. 2014, 20, 13188.
(f) Li, S. T.; Schnabel, T.; Lysenko, S.; Brandhorst, K.; Tamm, M. Chem. Commun. 2013, 49, 7189.
(g) Yang, H.; Jin, Y.; Du, Y.; Zhang, W. J. Mater. Chem. A 2014, 2, 5986.
(h) Heppekausen, J.; Stade, R.; Goddard, R.; Fürstner, A. J. Am. Chem. Soc. 2010, 132, 11045.
(i) Weissman, H.; Plunkett, K. N.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 585.
[4] For reviews on osmium carbyne complexes see:
(a) Bolaño, T.; Esteruelas, M. A.; Oñate, E. J. Organomet. Chem. 2011, 696, 3911.
(b) Jia, G.. Coord. Chem. Rev. 2007, 251, 2167.
(c) Roper, W. R. In Transition Metal Carbyne Complexes, Ed.:Kreissl, F. R., Kluwer Academic:Dordrecht, The Netherlands, 1993, 155.
(d) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
[5] Selected recent examples of osmium carbyne complexes:
(a) Casanova, N.; Esteruelas, M. A.; Gulías, M.; Larramona, C.; Mascareñas, J. L.; Oñate, E. Organometallics 2016, 35, 91.
(b) Zhou, X.; He, X.; Lin, J.; Zhuo, Q.; Chen, Z.; Zhang, H.; Wang, J.; Xia, H. Organometallics 2015, 34, 1742.
(c) Chen, J.; Huang, Z.-A.; Hua, Y.; Zhang, H.; Xia, H. Organometallics 2015, 34, 340.
(d) Buil, M. L.; Cardo, J. J. F.; Esteruelas, M. A.; Fernández, I.; Oñate, E. Organometallics 2015, 34, 547.
(e) Chen, J.; Zhang, C.; Xie, T.; Wen, T. B.; Zhang, H.; Xia, H. Organometallics 2013, 32, 3993.
(f) An, R.; Li, T.; Wen, T.-B. Chin. J. Org. Chem. 2013, 33, 1697(in Chinese).(安冉, 李亭, 温庭斌, 有机化学, 2013, 33, 1697.)
(g) Chen, J. X.; Sung, H. H. Y.; Williams, I. D.; Jia, G. Organometallics 2011, 30.
(h) Richter, B.; Werner, H. Organometallics 2009, 28, 5137.
(i) Bolaño, T.; Alba Collado, A.; Esteruelas, M. A.; Oñate, E. Organometallics 2009, 28, 2107.
(g) Castro-Rodrigo, R.; Esteruelas, M. A.; López, A. M.; Oñate, E. Organometallics 2008, 27, 3547.
(k) Castarlenas, R.; Esteruelas, M. A.; Lalrempuia, R.; Oliván, M.; Oñate, E. Organometallics 2008, 27, 795.
(l) Lee, J. H.; Pink, M.; Caulton, K. G. Organometallics 2006, 25, 802.
(m) Wen, T. B.; Hung, W. Y.; Zhou, Z. Y.; Lo, M. F.; Williams, I. D.; Jia, G. Eur. J. Inorg. Chem. 2004, 2837.
(n) Asensio, A.; Buil, M. L.; Esteruelas, M. A.; Oñate, E. Organometallics 2004, 23, 5787.
(o) Esteruelas, M. A.; López, A. M.; Oñate, E.; Royo, E. Organometallics 2004, 23, 3021.
(p) Wen, T. B.; Zhou, Z. Y.; Lo, M. F.; Williams, I. D.; Jia, G. Organometallics 2003, 22, 5217.
(q) Barrio, P.; Esteruelas, M. A.; Oñate, E. Organometallics 2003, 22, 2472.
(r) Weberndörfer, B.; Henig, G.; Hockless, D. C. R.; Bennett, M. A.; Werner, H. Organometallics 2003, 22, 744.
(s) Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2001, 20, 3283.
(t) Wen, T. B.; Cheung, Y. K.; Yao, J.; Wong, W. T.; Zhou, Z. Y.; Jia, G. Organometallics 2000, 19, 3803.
[6] (a) Buil, M. L.; Cardo, J. J. F.; Esteruelas, M. A.; Oñate, E. Organometallics 2016, 35, 2171.
(b) Buil, M. L.; Cardo, J. J. F.; Esteruelas, M. A.; Fernández, I.; Oñate, E. Organometallics 2014, 33, 2689.
(c) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Modrego, F. J.; Oñate, E. J. Am. Chem. Soc. 2005, 127, 11184.
(d) Barrio, P.; Esteruelas, M. A.; Oñate, E. J. Am. Chem. Soc. 2004, 126, 1946.
[7] (a) Jia, G. Organometallics 2013, 32, 6852 and references cited therein.
(b) Chen, J.; He, G.; Jia, G. Chin. J. Org. Chem. 2013, 33, 792(in Chinese).(陈江溪, 何国梅, 贾国成, 有机化学, 2013, 33, 792.)
(c) Chen, J.; Shi, C.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G.. Angew. Chem., Int. Ed. 2011, 50, 7295.
(d) Hung, W. Y.; Liu, B.; Shou, W.; Wen, T. B.; Shi, C.; Sung, H. H.-Y.; Williams, I. D.; Lin, Z.; Jia, G. J. Am. Chem. Soc. 2011, 133, 18350.
(e) He, G.; Zhu, J.; Hung, W. Y.; Wen, T. B.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Angew. Chem. Int. Ed. 2007, 46, 9065.
(f) Hung, W. Y.; Zhu, J.; Wen, T. B.; Yu, K. P.; Sung, H. H.-Y.; Williams, I. D.; Lin, Z.; Jia, G. J. Am. Chem. Soc. 2006, 128, 13742.
(g) Jia, G. Acc. Chem. Res. 2004, 37, 479.
[8] (a) Cao, X.-Y.; Zhao, Q.; Lin, Z.; Xia, H. Acc. Chem. Res. 2014, 47, 341.
(b) Chen, J.; Huang, Z.-A.; Lu, Z.; Zhang, H.; Xia, H. Chem. Eur. J. 2016, 22, 5363.
(c) Zhu, C.; Yang, Y.; Luo, M.; Yang, C.; Wu, J.; Chen, L.; Liu, G.; Wen, T.; Zhu, J.; Xia, H. Angew. Chem., Int. Ed. 2015, 54, 6181.
(d) Zhu, C.; Li, S.; Luo, M.; Zhou, X.; Niu, Y.; Lin, M.; Zhu, J.; Cao, Z.; Lu, X.; Wen, T.; Xie, Z.; Schleyer, P. V. R.; Xia, H. Nat. Chem. 2013, 5, 698.
(e) Liu, B.; Xie, H.; Wang, H.; Wu, L.; Zhao, Q.; Chen, J.; Wen, T. B.; Cao, Z.; Xia, H. Angew. Chem., Int. Ed. 2009, 48, 5461.
(f) Liu, B.; Wang, H.; Xie, H.; Zeng, B.; Chen, J.; Tao, J.; Wen, T. B.; Cao, Z.; Xia, H. Angew. Chem., Int. Ed. 2009, 48, 5430.
[9] Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4th ed., John Wiley & Sons, New York, 2005, pp. 309~340.
[10] (a) Mayr, A.; Asaro, M. F.; Kjelsberg, M. A.; Lee, K. S.; Van Engen, D. Organometallics 1987, 6, 432.
(b) Doyle, R. A.; Angelici, R. J. Organometallics 1989, 8, 2207.
(c) Blosch, L. L.; Abboud, K.; Boncella, J. M. J. Am. Chem. Soc. 1991, 113, 7066.
(d) Bastos, C. M.; Daubenspeck, N.; Mayr, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 743.
(e) Giannini, L.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. J. Am. Chem. Soc. 1998, 120, 823.
(f) Bannwart, E.; Jacobsen, H.; Furno, F.; Berke, H. Organometallics 2000, 19, 3605.
[11] Boone, M. P.; Brown, C. C.; Ancelet, T. A.; Stephan, D. W. Organometallics 2010, 29, 4369.
[12] Esteruelas, M. A.; López, A. M.; Oliván, M. Coord. Chem. Rev. 2007, 251, 795.
[13] (a) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2007, 26, 2037.
(b) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Oñate, E. J. Am. Chem. Soc. 2007, 129, 8850.
(c) Buil, M. L.; Esteruelas, M. A.; Garcés, K.; Oñate, E. Organometallics 2009, 28, 5691.
[14] (a) Esteruelas, M. A.; González, A. I.; López, A. M.; Oñate, E. Organometallics 2003, 22, 414.
(b) Esteruelas, M. A.; González, A. I.; López, A. M.; Oñate, E. Organometallics 2004, 23, 4858.
(c) Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2007, 26, 2129.
(d) Buil, M. L.; Esteruelas, M. A.; Garcés, K.; Oliván, M.; Oñate, E. Organometallics 2008, 27, 4680.
[15] Ozerov, O. V.; Watson, L. A.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2007, 129, 6003.
[16] Caulton, K. G. J. Organomet. Chem. 2001, 617~618, 56.
[17] (a) Ferrando, G.; Gérard, H.; Spivak, G. J.; Coalter Ⅲ, J. N.; Huffman, J. C.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 2001, 40, 6610.
(b) Ferrando-Miguel, G.; Gérard, H.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 2002, 41, 6440.
(c) Ferrando, G.; Coalter, J. N.; Gerard, H.; Huang, D.; Eisenstein, O.; Caulton, K. G. New J. Chem. 2003, 27, 1451.
(d) Grünwald, G.; Gevert, O.; Wolf, J.; González-Herrero, P.; Werner, H. Organometallics 1996, 15, 1960.
[18] (a) Espuelas, J.; Esteruelas, M. A.; Lahoz, F. J.; Oro, L. A.; Ruiz, N. J. Am. Chem. Soc. 1993, 115, 4683.
(b) Collado, A.; Esteruelas, M. A.; López, F.; Mascareñas, J. L.; Oñate, E.; Trillo, B. Organometallics 2010, 29, 4966.
(c) Collado, A.; Esteruelas, M. A.; Oñate, E. Organometallics 2011, 30, 1930.
[19] Spivak, G. J.; Coalter, J. N.; Olivan, M.; Eisenstein, O.; Caulton, K. G. Organometallics 1998, 17, 999.
[20] (a) Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746.
(b) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
(c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
[21] Grubbs has reported the reaction of OsCl2(PPh3)3 with diphenylcyclopropene to afford OsCl2(=CHCH=CPh2)(PPh3)2, but no experimental evidence has been given, see:
(a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974.
(b) Grubbs, R. H.; Schwab, P.; Nguyen, S. T. WO 9706185, 1997[Chem. Abstr. 1997, 126, 238816].
[22] Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
[23] (a) Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofmann, P. J. Organomet. Chem. 2002, 641, 220.
Related syntheses of a series of ruthenium alkenylcarbenes RuCl2(=CHCH=CR1R2)(dtbpm) with a chelating ligand bis(di-tert-butyl-phosphanyl)methane t-Bu2PCH2Pt-Bu2(dtbpm) from the reactions of a dinuclear ruthenium hydride[RuH(μ2-Cl)-(dtbpm)]2 with propargylic chlorides HC≡CC(Cl)R1R2 have also been reported by Hofmann:
(b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofmann, P. Chem.-Eur. J. 1999, 5, 557.
(c) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofmann, P. Angew. Chem., Int. Ed. 1999, 38, 1273.
[24] Amoroso, D.; Snelgrove, J. L.; Conrad, J. C.; Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Adv. Synth. Catal. 2002, 344, 757.
[25] Werner, H.; Jung, S.; Weberndörfer, B.; Wolf, J. Eur. J. Inorg. Chem. 1999, 1999, 951.
[26] Ferrando, G.; Caulton, K. G. Inorg. Chem. 1999, 38, 4168.
[27] (a) Bustelo, E.; Jiménez-Tenorio, M.; Mereiter, K.; Puerta, M. C.; Valerga, P. Organometallics 2002, 21, 1903.
(b) Esteruelas, M. A.; Oliván, M.; Oñate, E. Organometallics 1999, 18, 2953.
(c) Crochet, P.; Esteruelas, M. A.; López, A. M.; Martinez, M. P.; Oliván, M.; Oñate, E.; Ruiz, N. Organometallics 1998, 17, 4500.
[28] (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
(b) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
[29] (a) Wen, T. B.; Yang, S. Y.; Zhou, Z. Y.; Lin, Z.; Lau, C. P.; Jia, G. Organometallics 2000, 19, 3757.
(b) Wen, T. B.; Zhou, Z. Y.; Jia, G. Angew. Chem., Int. Ed. 2001, 40, 1951.
(c) Wen, T. B.; Hung, W. Y.; Sung, H. H. Y.; Williams, I. D.; Jia, G. J. Am. Chem. Soc. 2005, 127, 2856.
(d) Wen, T. B.; Lee, K.-H.; Chen, J.; Hung, W. Y.; Bai, W.; Li, H.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Organometallics 2016, 35, 1514.
[30] Collado, A.; Esteruelas, M. A.; López, F.; Mascareñas, J. L.; Oñate, E.; Trillo, B. Organometallics 2010, 29, 4966.
[31] Spivak, G. J.; Caulton, K. G. Organometallics 1998, 17, 5260.
[32] Hoffmann, P. R.; Caulton, K. G. J. Am. Chem. Soc. 1975, 97, 4221.
[33] Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4099.
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