Boron containing 1,1-Dimetallicalkane Reagents
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1 Boron containing 1,1-Dimetallicalkane Reagents Topic Talk Xun Liu July 25, 2013
2 Outline 1. 1,1-Borio-lithioalkane reagents 2. 1,1-Boronalkane reagents 3. 1,1-Borio-zincioalkane Reagents and 1,1-Borio-cuprioalkane Reagents 4. 1,1-Borio-zirconioalkane Reagents 5. 1,1-Borio-siliconioalkane Reagents
3 1,1-Borio-lithioalkane reagents Preparation: 1,Use bulky base to generate 2,use bulky boron Rathke, M. W.; Kow, R. J. Am. Chem. Soc. 1972, 94, Pelter, A.; Singaram, B.; Williams, L.; Wilson, J. W. Tetrahedron Lett. 1983, 24, 623.
4 1,1-Borio-lithioalkane reagents Boron alkylation and boron wittig reaction: Matteson, D. S.; Moody, R. J. Organometallics 1982, 1, 20. Matteson,D.S.;Arne,K.H.J.Am.Chem.Soc.1978,100,1325.
5 1,1-Borio-lithioalkane reagents Boron wittig reaction: Pelter, A.; Buss, D.; Pitchford, A. Tetrahedron Lett. 1985, 26, Pelter, A.; Peverall, S.; Pitchford, A. Tetrahedron 1996, 52, 1085.
6 1,1-Borio-lithioalkane reagents Boron wittig reaction: Pelter, A.; Buss, D.; Cocllough, E. J. Chem. Soc., Chem. Commun. 1987, 297. Pelter, A.; Buss, D.; Cocllough, E.; Singaram, B. Tetrahedron 1993, 49, 7077
7 1,1-Borio-lithioalkane reagents Boron wittig reaction: Pelter, A.; Smith, K.; Elgendy, S.; Rowlands, M. Tetrahedron Lett. 1989, 30, Pelter, A.; Smith, K.; Elgendy, S. M. A.; Rowlands, M. Tetrahedron , 7104.
8 1,1-Borio-lithioalkane reagents Epoxidation reaction: Pelter, A.; Bugden, G.; Rosser, R. Tetrahedron Lett. 1985, 26, Pelter, A.; Vaughan-Williams, G. F.; Rosser, R. M. Tetrahedron 1993, 49, 3007.
9 1,1-Borio-lithioalkane reagents Nucleophilic Addition of Unsaturated Boranes Cooke, M. P., Jr.; Widener, R. K. J. Am. Chem. Soc. 1987, 109, 931. Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495.
10 1,1-Borio-lithioalkane reagents Allylic 1,1 borio-lithio: Pelter, A.; Singaram, B.; Wilson, J. W. Tetrahedron Lett. 1983, 24, 631.
11 1,1-Borio-lithioalkane reagents Vinyl 1,1 borio-lithio: Kow, R.; Rathke, M. W. J. Am. Chem. Soc. 1973, 95, 2715.
12 Preparation: 1. 1,1-Diboronalkane reagents 2. Brown, H. C.; Zweifel, G. J. Am. Chem. So. 1961, 83, % Endo,K.;Hirokami,M.;Shibata,T.Synlett 2009,
13 1,1-Diboronalkane reagents Preparation: 3 4 Lee, J. ; McDonald, R.; Hall, D. Nature chemistry, 2011, 894 Feng, X.; g Jeon, H.; Yun, J. Angew. Chem. Int. Ed. 2013, 52,
14 1,1-Diboronalkane reagents Our Preparation:
15 1,1-Diboronalkane reagents Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 291
16 1,1-Diboronalkane reagents Intramolecular alkylation reaction: Brown, H. C.; Rhodes, S. P. J. Am. Chem. Soc. 1969, 91, 4306.
17 1,1-Diboronalkane reagents Intermolecular Alkylation reaction: 75% Zweifel, G.; Arzoumanian, H. Tetrahedron Lett. 1966, 2535
18 1,1-Diboronalkane reagents Proposed Mechanism of alkylation based on NMR: LiMe: -2.1ppm, not observed, ate complex: -0.7 and -0.8 ppm, observed 75% After rxn, only 15% complex left Zweifel, G.; Fisher, R. P.; Horng, A. Synthesis 1973, 37
19 1,1-Diboronalkane reagents Deboroacylation reaction: Mukaiyama, T.; Murakami, M.; Oriyama, T.; Yamaguchi, M. Chem. Lett 1981, 1193.
20 1,1-Diboronalkane reagents Acylation reaction: Cainelli, G.; Dal Bello, G.; Zubiani, G. Tetrahedron Lett. 1966, J. Org. Chem. 2010, 75,
21 1,1-Diboronalkane reagents Cross coupling: Fast transmetalation No B-hydride elimination J. AM. CHEM. SOC. 2010, 132,
22 1,1-Diboronalkane reagents Cross coupling: J. Org. Chem. 2012, 77, J. Org. Chem. 2012, 77,
23 1,1-Diboronalkane reagents Enantioselective cross coupling: Lee, J. ; McDonald, R.; Hall, D. Nature chemistry, 2011, 894
24 1,1-Diboronalkane reagents Protodeboronation phenomenon: 64% Dulou, R.; Chretien-Bessie`re, Y. Bull. Soc. Chim. Fr. 1959, 1362 Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 291
25 1,1-Borio-zincioalkane Reagents Preparation: Knochel, P. J. Am. Chem. Soc. 1990, 112, Rozema, M. J.; Sidduri, A. R.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
26 1,1-Borio-zincioalkane Reagents Cross coupling reaction and allylation: Watanabe, T.; Miyaura, N.; Suzuki, A. J. Organomet. Chem. 1993, 444, C1.
27 1,1-Borio-zincioalkane Reagents Cross coupling and allylation reaction: Watanabe,T.;Sakai,M.;Miyaura,N.;Suzuki,A.J.Chem.Soc., Chem. Commun. 1994, 467.
28 1,1-Borio-zincioalkane Reagents Cross coupling and Diels Alder reaction: Kanai, G.; Miyaura, N.; Suzuki, A. Chem. Lett. 1993, 845.
29 1,1-Borio-cuprioalkene Reagents Knochel, P. J. Am. Chem. Soc. 1990, 112, Gridnev,I.;Kanai,G.;Miyaura,N.;Suzuki,A.J.Organomet. Chem. 1994, 481, C4. Sakai, M. Saito, S.; Kanas, G.; Suzuki, A.; Miyaura, N. Tetrahedron 1996, 52, 915.
30 1,1-Borio-zirconioalkane Reagents Preparation: Zheng, B.; Srebnik, M. Tetrahedron Lett. 1993, 34, Hartner, F. W. Jr.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979.
31 1,1-Borio-zirconioalkane Reagents Copper reactions: Zheng, B.; Srebnik, M. J. Org. Chem. 1995, 60, 486. Pereira, S.; Srebnik, M. Tetrahedron Lett. 1995, 36, Zheng, B.; Srebnik, M. Tetrahedron Lett. 1995, 36, Deloux, L.; Srebnik, M. Tetrahedron Lett. 1996, 37, 2735.
32 1,1-Borio-zirconioalkane Reagents Diastereoselective hydrozirconation: Pereira, S.; Srebnik, M. Tetrahedron Lett. 1994, 35, 6247.
33 1,1 boronsilicon Reagents Preparation: Angew. Chem. Int. Ed. 2001, 40, 4283 Carosi, L.; Lachance, H.; Hall, D. G. Tetrahedron Letters 2005,
34 1,1 boronsilicon Reagents Reaction: Carosi, L.; Lachance, H.; Hall, D. G. Tetrahedron Letters 2005,
35 Summary Because the gem dimetals have different reacitivities, they can be used for alkylation, acylation and cross coupling reactions chemselectivily, and these compounds can be readily converted into alcohols, amines, and carboxylic acids, and also used for the formation of C C bond, which shows great research future.
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