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Synthesis 2016; 48(19): 3155-3164
DOI: 10.1055/s-0035-1561670
DOI: 10.1055/s-0035-1561670
paper
Orthogonally Reacting Boron Coupling Reagents: A Novel Multicomponent-Multicatalytic Reaction [(MC)2R] of Dichlorovinylpyrazine
Further Information
Publication History
Received: 03 April 2016
Accepted after revision: 09 May 2016
Publication Date:
21 June 2016 (online)
Abstract
The results presented herein illustrate the feasibility of two orthogonally reacting boron coupling reagents as a new control strategy in multicomponent-multicatalytic reaction [(MC)2R] chemistry. A process employing dichlorovinylpyrazine merging the rhodium-catalyzed hydroarylation with the Suzuki coupling has been discovered. Three new bonds are formed in a one-pot, one-step process efficiently providing highly substituted diaza-dihydrodibenzoxepine products.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561670.
- Supporting Information
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References
- 1 Pàmies O, Bäckvall J.-E. Chem. Rev. 2003; 103: 3247
- 2 Rueping M, Koenigs RM, Atodiresei I. Chem. Eur. J. 2010; 16: 9350
- 3a Park YJ, Park J.-W, Jun C.-H. Acc. Chem. Res. 2008; 41: 222
- 3b Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
- 3c Zhong C, Shi X. Eur. J. Org. Chem. 2010; 2999
- 4a Lee JM, Na Y, Han H, Chang S. Chem. Soc. Rev. 2004; 33: 302
- 4b Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
- 4c Ambrosini LM, Lambert TH. ChemCatChem 2010; 2: 1373
- 5 Hansmann MM, Hashmi AS. K, Lautens M. Org. Lett. 2013; 15: 3226
- 6a Zhang L, Qureshi Z, Sonaglia L, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 13850
- 6b Zhang L, Panteleev J, Lautens M. J. Org. Chem. 2014; 79: 12159
- 7 Friedman AA, Panteleev J, Tsoung J, Huynh V, Lautens M. Angew. Chem. Int. Ed. 2013; 52: 9755
- 8a Gillis EP, Burke MD. Aldrichimica Acta 2009; 42: 17
- 8b Molander GA, Sandrock DL. J. Am. Chem. Soc. 2008; 130: 15792
- 8c Yamashita Y, Tellis JC, Molander GA. Proc. Natl. Acad. Sci. U.S.A. 2015; 112: 12026
- 8d Seath CP, Fyfe JW. B, Molloy JJ, Watson AJ. B. Angew. Chem. Int. Ed. 2015; 54: 9976
- 8e Fyfe JW. B, Seath CP, Watson AJ. B. Angew. Chem. Int. Ed. 2014; 45: 12077
- 9a Lautens M, Roy A, Fukuoka K, Fagnou K, Martin-Matute B. J. Am. Chem. Soc. 2001; 123: 5358
- 9b Pattison G, Piraux G, Lam HW. J. Am. Chem. Soc. 2010; 132: 14373
- 9c Roy ID, Burns AR, Pattison G, Michel B, Parker AJ, Lam HW. Chem. Commun. 2014; 50: 2865
- 9d Saxena A, Lam HW. Chem. Sci. 2011; 2: 2326
- 10 Nikishkin NI, Huskens J, Verboom W. Org. Biomol. Chem. 2013; 11: 3583
- 11a Batey RA, Quach TD. Tetrahedron Lett. 2001; 42: 9099
- 11b Molander GA, Biolatto B. Org. Lett. 2002; 4: 1867
- 11c Molander GA, Biolatto B. J. Org. Chem. 2003; 68: 4302
- 11d Yuen AK. L, Hutton CA. Tetrahedron Lett. 2005; 46: 7899
- 11e Gendrineau T, Genet JP, Darses S. Org. Lett. 2009; 11: 3486
- 11f Gillis EP, Burke MD. J. Am. Chem. Soc. 2007; 129: 6716
- 11g Knapp DM, Gillis EP, Burke MD. J. Am. Chem. Soc. 2009; 131: 6961
- 11h Molander GA, Ito T. Org. Lett. 2001; 3: 393
- 11i Lennox AJ. J, Lloyd-Jones GC. J. Am. Chem. Soc. 2012; 134: 7431
- 12a Carrow BP, Hartwig JF. J. Am. Chem. Soc. 2011; 133: 2116
-
12b Fujii S, Chang SY, Burke MD. Angew. Chem. Int. Ed. 2011; 50: 7862
- 13 Kina A, Iwamura H, Hayashi T. J. Am. Chem. Soc. 2006; 128: 3904
- 14a Miyaura N. Bull. Chem. Soc. Jpn. 2008; 81: 1535
- 14b Itooka R, Iguchi Y, Miyaura N. J. Org. Chem. 2003; 68: 6000
- 15a Torssell T In Progress in Boron Chemistry . Steinberg H, McCloskey AL. Pergamon; New York: 1964
- 15b Kuivila HG, Keough AH, Soboczenski EJ. J. Org. Chem. 1954; 8: 780
- 15c Bowie RA, Musgrave OC. J. Chem. Soc., Chem. Commun. 1963; 3945
- 16 Darses S, Michaud G, Genêt JP. Eur. J. Org. Chem. 1999; 8: 1875
- 17 Friedman AA. Rhodium and Palladium Catalyzed Domino Reaction of Alkenyl Pyridines and Alkenyl Pyrazines . Master’s Thesis University of Toronto; Canada: 2013
- 18a Oliveira RA, Silva RO, Molander GA, Menezes PH. Magn. Reson. Chem. 2009; 47: 873
- 18b Peters M, Trobe M, Tan H, Kleineweischede R, Breinbauer R. Chem. Eur. J. 2013; 19: 2442
- 18c Molander GA, Trice SL. J, Kennedy SM, Dreher SD, Tudge MT. J. Am. Chem. Soc. 2012; 134: 11667
- 18d Molander GA, Cavalcanti LN, García C. J. Org. Chem. 2013; 78: 6427
- 18e Smoum R, Rubinstein A, Srebnik M. Org. Biomol. Chem. 2005; 3: 941
- 18f Vedejs E, Chapman RW, Fields SC, Lin S, Schrimpf MR. J. Org. Chem. 1995; 60: 3020
- 18g Molander GA, Bernardi CR. J. Org. Chem. 2002; 67: 8424
- 19 Turck A, Trohay D, Mojovic L, Plé N, Quéguiner G. J. Organomet. Chem. 1991; 412: 301