Review. Recent Developments in Pd-catalyzed Carbonylation Reaction. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang
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1 Review Recent Developments in Pd-catalyzed Carbonylation Reaction Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang
2 History 1962, E. Fischer Z. Nafurforsch. 1962, 17b, , R. Heck J. Org. Chem. 1972, 37(14), , Heck reaction 1974, R. Heck J. Org. Chem. 1974, 39(23), /39
3 Mechanism Migration or Insertion? Assume: No trans-insertion No stereo-wobbling 3/39
4 Mechanism Migration or Insertion? K. Noack And F. Calderazzo, J. Organometal. Chem. 1967, 10, /39
5 Mechanism Migration or Insertion? B. Scott Williams, et. al., Organometallics 2009, 28, Exception Gordon. K. Anderson, et. al., Acc. Chem. Res. 1984,17, /39
6 Mechanism Mostly dissociation-insertion (3/4-coordinate, not 4/5) Non-RDS fast process Kinetic study of >100 rxn of Ni, Pd, Pt. R.F. Heck, et. al., J. Am. Chem. Soc., 1976, 98, Exception Excessed or firm ligands C.H. Stam, et. al., Inorg. Chim. Acta, 1990, 169, 5. 6/39
7 Influencing factors CO substitution Electronic migrating R Nucleophilicity CO Pressure Sterically hindered P t Bu 3, BuPAd 2, bulky NHC Throw-away ligend (L) Py, MeCN > PR 3 > AcO -, Cl - R: n-alkyl anion > allylic, benzylic Ar: electron rich > electron poor Trans effect on R Trapping ligand Trans-effect / Pi-pushing effect Electronic CO δ + CO Ion effect: Li + > Na + Lewis acid Favor strong coordination ligand PMe 3 > PMe 2 Ph > PMePh 2 > CO Nucleophile / Bidentate ligand Binding angle Edward S. Petrov, et. al., React. Kinet. Catal. Lett., 1998, 64, 359. S. Sakaki, et.al., J. Am. Chem. Soc. 1983, 105, Kingsley J. Cavel, Coord. Chem. Rev. 1996, 155, 209. Tao Tu, et.al., Synthesis 2014, 46, /39
8 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 8/39
9 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 9/39
10 C(sp) Pd Takahashi, T. et. al., Tetrahedron Lett. 1980, 21, 849. Takahashi, T. et. al., Tetrahedron Lett. 1980, 21, 849. Ishii, Y et. al.,. Tetrahedron Lett. 1999, 40, Ishii, Y et. al.,. Tetrahedron Lett. 1999, 40, /39
11 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 11/39
12 C(sp 2 ) Pd 12/39
13 C(sp 2 ) Pd Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 卿凤翎, et.al. J. Fluorine Chem. 2002, 114, 177. Hamel, N. et. al., Tetrahedron Lett. 1987, 28, Ban, Y. et. al., J. Chem. Soc., Chem. Commun. 1979, 698. Ban, Y. et. al., Tetrahedron 1985, 41, /39
14 C(sp 2 ) Pd Chiusoli, G. P. et. al., J. Chem. Soc., Perkin Trans , 147. Norton, J. R. et. al., J. Am. Chem. Soc. 1981, 103, Dupont, J. et. al., Tetrahedron Lett. 2002, 43, 753. 赵世民, et. al., J. Org. Chem. 2005, 70, /39
15 C(sp 2 ) Pd Hirao, T. et. al., J. Org. Chem. 1997, 62, Gabriele, B. et. al.,; Adv. Synth. Catal. 2004, 346, 351. Gabriele, B. et. al., Synthesis 2007, /39
16 C(sp 2 ) Pd Larock, R. C. et. al., J. Org. Chem. 2004, 69, BILN 2061 Haddad, N.; Tan, J.; Farina, V. J. Org. Chem. 2006, 71, /39
17 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 17/39
18 C(sp 3 )-Pd Danishefsky, S. et. al.; Tetrahedron Lett. 1983, 24, 15. Yoshida, Z. et. al., J. Am. Chem. Soc. 1988, 110, Danishefsky, S et. al.; Tetrahedron Lett. 1983, 24, 15. Yoshida, Z. et. al., J. Am. Chem. Soc. 1988, 110, /39
19 C(sp 3 )-Pd Ilhyong Ryu, et. al., Acc. Chem. Res. 2014, 47, /39
20 Beyond small ring Cao, H.; Vieira, T. O. et. al.,; Alper, H. Org. Lett. 2011, 13, 11. Chouhan, G.; Alper, H. et. al., Org. Lett. 2010, 12, 192. Lenoble, G.; Urrutigoity, M.; Kalck, P. et. al., Tetrahedron Lett. 2001, 42, /39
21 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook 21/39
22 Double Carbonylation Aklo Yamamoto, et. al., Tetrahedron Lett., 1982, 23, ; J. Am. Chem. Soc., 1985, 107, M. Tanaka, et. al., J. Organomet. Chem., 1982, 233, C64 C66. (11 days later) 22/39
23 Double Carbonylation T. Watanabe, et. al., J. Org. Chem., 2001, 66, /39
24 Double Carbonylation Yoshinori Kondo, et. al., Chem. Commun., 2006, /39
25 Double Carbonylation Takashi Takahashi, et. al., Tetrahedron, 2015, 71, /39
26 Outlook Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook 26/39
27 C-H Carbonylation Alkoxycarbonylation Aryl C(sp 2 )-H Booker-Milburn, K. I., Angew. Chem., Int. Ed. 2009, 48, Shi, Z.-J. Dalton Trans. 2010, 39, /39
28 C-H Carbonylation Lei, A.-W. Chem. Eur. J. 2011, 17, 李福伟, et.al. Org. Lett. 2012, 14, /39
29 C-H Carbonylation Yu, J.-Q. Chem. Sci. 2011, 2, Shi, B.-F. Synlett. 2013, 24, Shi, B.-F. Org. Biomol. Chem. 2014, 12, Shih-Ching Chuang, Chem. Commun. 2013, 49, /39
30 C-H Carbonylation Huang, H. ( 黄汉民 ) J. Am. Chem. Soc. 2012, 134, Huang, H., et. al. Org. Lett., 2013, 15 (13), /39
31 C-H Carbonylation Inert C(sp3)-H carbonylation Fujiwara, Y., et. al. Chem. Lett. 1989, Fujiwara, Y., et. al. Chem. Lett. 1992, 1141 Fujiwara, Y., et. al. Organomet. Chem. 1994, 473, 329. Fujiwara, Y., et. al. Chem. Lett. 1991, 1433 Fujiwara, Y., et. al. Org. Lett. 1999, /39
32 C-H Carbonylation Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, Matthew J. Gaunt, Nature 2014, 510, /39
33 C-H Carbonylation Xi-Sheng Wang, Org. Lett. 2015, 17, /39
34 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook All carbon skeleton / ring system 34/39
35 All carbon skeleton Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, Y. Zhao, L. Jin, P. Li, A. Lei, J. Am. Chem. Soc. 2008, 130, /39
36 All carbon skeleton Beller, M. Chem. Asian J. 2012, 7, S.-C. Choi, Synth. Commun. 2001, 31, Hiroaki Sasai, et. al., Synlett 2009, R. F. W. Jackson, J. Chem. Soc. Perkin Trans , /39
37 All carbon ring system Wolfgang Oppolzer, et. al., Helvetica Chimica Acta, 1991, 74, 465 By Dr. You Lin, 2012 Jiahua Chen, and Zhen Yang, et. al., Org. Lett. 2005, 7, Jia-Hua Chen, Aiwen Lei, Zhen Yang, et..al., Synthesis, 2007, 16, Zhen Yang, and Yun-Dong Wu, et. al., J. Org. Chem. 2009, 74, /39
38 All carbon ring system Other examples? Why rare? Chuangchuang Li, and Zhen Yang, Chem. Asian J. 2013, 8, /39
39 Acknowledgements Prof. Yang, Prof. Chen, Prof. Tang Mr. You Lin B630 Everyone in Lab. and everyone here Ac 39/39
40 Supplement Lenoble, G.; Urrutigoity, M.; Kalck, P. Tetrahedron Lett. 2001, 42, 3697 Yu Bai, Dexter C. Davis, and Mingji Dai, Angew. Chem. Int. Ed. 2014, 53, /39
41 Regioselectivity of Allene Cyclocarbonylation Selective allylic substitution at more substituted site Ye, F.; Alper, H. J. Org. Chem. 2007, 72, Richard C. Larock* and John M. Zenner, J. Org. Chem. 1995, 60, /39
42 Sequence Selectivity Larock, R. C. J. Org. Chem. 2004, 69, Yang, Q.; Alper, H. J. Org. Chem. 2010, 75, 948. Xuefeng Jiang*, et. al., Angew. Chem. Int. Ed. 2015, 54, /39
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