Synthetically useful extrusion reactions in organic chemistry
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1 Synthetically useful extrusion reactions in organic chemistry Reporter: Sun Baochuan Supervisors: Prof. Yang Zhen Prof. Chen Jiahua
2 Extrusion Reactions Extrusion Reaction: An atom or group Y connected to two other atoms X and Z is lost from a molecule, leading to a product in which X is bonded directly to Z. Y: Typically small, stable, inorganic molecules or atoms SO 2, S, N 2, CO 2, COS, CO, O 2, Se Guziec, F. S.; Sanfilippo, L. J. Tetrahedron. 1988, 44, Smith, M. B.; March, J. In Advanced Organic Chemistry. 6 th ed.; Wiley: Hoboken, 2007; P1553. Jones, R. A. Y.; Bunnett, J. F. Pure & Appl. Chem. 1989, 61,
3 Extrusion Reactions Extrusion of SO 2 (Mechanism and Example) The Ramberg - Bäcklund Reaction (RBR) Extrusion of S (Mechanism and Example) Eschenmoser Coupling Reaction (ECR) Other Extrusion Reactions Twofold Extrusion Reactions Acknowledgement
4 Extrustion of SO 2 Y = SO 2 Conditions: Pyrolysis Photolysis Base (The Ramberg-Bäcklund Reaction) Mechanism: Pyrolysis (radical) Mechanism: Pyrolysis (cheletropic) McGregor, S. D.; Lemal, D. M. J. Am. Chem. Soc. 1966, 88, Vogtle, F.; Rossa, L. Angew. Chem. Int. Ed. Engl. 1979, 18, 515. Busfield, W. K.; Ivin, K. J. Trans. Faraday. Soc. 1961, 57, Mock, W. L. J. Am. Chem. Soc. 1969, 91, Kerr, J. A. Chem. Rev. 1966, 66,
5 Extrustion of SO 2 Mechanism: Photolysis (radical) Givens, R. S.; Hrinczenko, B.; Liu, J. H.-S.; Matuszewski, B.; Joan T.-C. J. Am. Chem. Soc. 1984, 106, Mechanism: Base (discussed in RBR) Examples: Cava, M. P.; Deana, A. J. Am. Chem. Soc. 1959, 81,
6 Extrustion of SO 2 Examples: Examples: Pettus, T. R. R.; Mejorado, L. H. J. Am. Chem. Soc. 2006, 128, Vogtle, F.; Bieber, W. Angew. Chem. Int. Ed. Engl. 1977, 16, 175. Vogtle, F.; Rossa, L. Angew. Chem. Int. Ed. Engl. 1979, 18,
7 Extrustion of SO 2 The Ramberg-Bäcklund Reaction (RBR) Modification: Meyers Chan s Others Meyers, C. Y.; Malte, A. M.; Mattews, W. S. J. Am. Chem. Soc. 1969, 91, Chan, T.-L.; Fong, S.; Li, Y.; Man, T.-O.; Poon, C.-D. J. Chem. Soc., Chem. Commun. 1994, 15,
8 Extrustion of SO 2 Mechanism: Bordwell, F. G.; Cooper, G. D. J. Am. Chem. Soc. 1951, 73, Taylor, J. K.; Sutherland, A. G. Tetrahedron Lett. 1989, 30, Bordwell, F. G.; Williams, J. M.; Hoyt, E. B.; Jarvis, B. B. J. Am. Chem. Soc. 1968, 90,
9 Extrustion of SO 2 Stereochemistry: Harvey, J. E. In Molecular Rearrangements in Organic Synthesis; Rojas, C. M., Ed.; J. Wiley & Sons: New York, Beker, K. B.; Labhart, M. P. Helvetica Chimica Acta. 1983, 66,
10 Extrustion of SO 2 Examples: disubstituted acyclic alkene Chow, H.-F.; Ng, M.-K.; Leung, C.-W.; Wang, G.-X. J. Am. Chem. Soc. 2004, 126,
11 Extrustion of SO 2 Examples: trisubstituted acyclic alkene Taylor, J. K.; Foot, J. S.; Giblin, M. P. Org. Lett. 2003, 5,
12 Extrustion of SO 2 Examples: polyunsaturated system Koo, S.; Choi, Seyoung, C. J. Org. Chem. 2005, 70,
13 Extrustion of SO 2 Examples: strained cyclic alkenes Boeckman, R. K.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, Cao, X-P.; Wang X-L.; Yang, Y-Y. J. Chem. Soc., Perkin Trans. 1, 2002,
14 Extrusion Reactions Extrusion of SO 2 (Mechanism and Example) The Ramberg - Bäcklund Reaction (RBR) Extrusion of S (Mechanism and Example) Eschenmoser Coupling Reaction (ECR) Other Extrusion Reactions Twofold Extrusion Reactions Acknowledgement
15 Extrusion Of S Y = S Conditions: Pyrolysis Photolysis Thiophile Mechanism: Pyrolysis Harpp, D. N.; Chew, W. Tetrahedron Lett. 1992, 33, 45. Lutz, E.; Biellmann, J.-F. Tetrahedron Lett. 1985, 26,
16 Extrusion Of S Mechanism: Thiophile Example: Bordwell, F. G.; Neureiter, N. P. J. Am. Chem. Soc. 1958, 81, 578. Denney, D. B.; Boskin, M. J. Am. Chem. Soc. 1960, 82, Murata, I.; Nakasuji, K. Top. Curr. Chem. 1981, 97, 33. Gleiter, R.; Krennrich, G.; Cremer, D.; Yamamoto, K.; Murata, I. J. Am. Chem. Soc. 1985, 107,
17 Extrusion Of S The Eschenmoser Coupling Reaction (ECR) Knott & Eschenmoser Mechanism: Alkylative coupling version Oxidative coupling version Alkylative coupling version 17
18 Extrusion Of S Complication: Brown, F. B.; Ireland, R. E. J. Org. Chem. 1980, 45, Rapoport, H.; Shiosaki, K.; Fels, G. J. Org. Chem. 1981, 46, Hart, D. J.; Sun, L.-Q. Tetrahedron, Lett. 1995, 36,
19 Extrusion Of S Examples: Hiemstra, H.; Louwrier, S.; Ostendorf, M.; Tuynman, A. Tetrahedron Lett. 1996, 37, 905. Michael, J. P.; Jungmann, C. M. Tetrahedron 1992, 48, Young, D. W.; Davies, D. E.; Doyle, P. M.; Hill, R. D. Tetrahedron 2005, 61,
20 Extrusion Of S Examples: Yamasaki, T.; Kadoi, H.; Nagakura, I. Heterocycles 1997, 45,
21 Extrusion Reactions Extrusion of SO 2 (Mechanism and Example) The Ramberg - Bäcklund Reaction (RBR) Extrusion of S (Mechanism and Example) Eschenmoser Coupling Reaction (ECR) Other Extrusion Reactions Twofold Extrusion Reactions Acknowledgement
22 Other Extrusion Reactions Extrusion of N 2 : Corey, E. J.; Mascitti V. J. Am. Chem. Soc. 2004, 126,
23 Other Extrusion Reactions Route to Precursor: Movassaghi, M.; Ahmad, O. K.; Lathrop, S. P. J. Am. Chem. Soc. 2011, 133,
24 Other Extrusion Reactions Route to Precursor: Movassaghi, M.; Ahmad, O. K.; Lathrop, S. P. J. Am. Chem. Soc. 2011, 133,
25 Other Extrusion Reactions Extrusion of COS: Extrusion of CO 2 : Padwa, A.; Bobeck, D. R.; Lee, H. I.; Flick, A. C. J. Org. Chem. 2009, 74, Baran, P. S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 128,
26 Extrusion Reactions Extrusion of SO 2 (Mechanism and Example) The Ramberg - Bäcklund Reaction (RBR) Extrusion of S (Mechanism and Example) Eschenmoser Coupling Reaction (ECR) Other Extrusion Reactions Twofold Extrusion Reactions Acknowledgement
27 Twofold Extrusion Reactions Guziec, L. J.; Guziec, F. S.; Organic Reactions. 2012, 78,
28 Twofold Extrusion Reactions Guziec, L. J.; Guziec, F. S.; Organic Reactions. 2012, 78,
29 Summary Extrusion of SO 2 Other Extrusion Reactions (N 2, CO 2, COS) Extrusion Reactions Extrusion of S Twofold Extrusion Reactions Advantage: Thermodynamic (SO 2, N 2, CO 2, COS) Application: Traceless Linker & Strained bonds
30 Acknowledgement Prof. Yang, Prof. Chen All professors in IOC J & K Everyone in my lab Everyone here Thanks for your attention!
31 From Baran Group Meeting
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