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. 2017 Jun 29;53(53):7270-7273.
doi: 10.1039/c7cc00997f.

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

Sébastien Laulhé  1 , J Miles Blackburn, Jennifer L Roizen
Affiliations

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

Sébastien Laulhé et al. Chem Commun (Camb). .

Abstract

A novel Suzuki-Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.

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Figures

Figure 1
Figure 1
Utility of the 2-alkylpyridines,
Scheme 1
Scheme 1
Prior disclosures and these investigations
Scheme 2
Scheme 2
Application to the synthesis of a dumbbell shaped molecule for a rotaxane
See this image and copyright information in PMC

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References

    1. Schinz H, Ruzicka L, Geyer U, Prelog V. Helv Chim Acta. 1946;29:1524.
    2. Fürstner A, Leitner A. Angew Chem Int Ed. 2003;42:308. - PubMed
    3. Davis JM, Truong A, Hamilton AD. Org Lett. 2005;7:5405. - PubMed
    4. Goldup SM, Leigh DA, Lusby PJ, McBurney RT, Slawin AMZ. Angew Chem Int Ed. 2008;47:6999. - PubMed
    5. Zhang YH, Shi BF, Yu JQ. J Am Chem Soc. 2009;131:5072. - PMC - PubMed
    6. Goetz AE, Garg NK. Nature Chemistry. 2013;5:54. - PMC - PubMed

    1. For select C–H activation processes, see:

    2. Lewis JC, Bergman RG, Ellman JA. J Am Chem Soc. 2007;129:5332. - PMC - PubMed
    3. Nakao Y, Yamada Y, Kashihara N, Hiyama T. J Am Chem Soc. 2010;132:13666. - PubMed

    4. For select examples that involve distinct bond-forming and deprotonation steps, see:

    5. Jeffrey JL, Sarpong R. Org Lett. 2012;14:5400. - PMC - PubMed
    6. Chen Q, León T, Knochel P. Angew Chem Int Ed. 2014;53:8746. - PubMed
    7. Hyodo I, Tobisu M, Chatani N. Chem Asian J. 2012;7:1357. - PubMed

    8. For select Minisci type-pathways, see:

    9. Jin J, MacMillan DWC. Nature. 2015;525:87. - PMC - PubMed
    10. Gianatassio R, Kawamura S, Eprile CL, Foo K, Ge J, Burns AC, Collins MR, Baran PS. Angew Chem Int Ed. 2014;53:9851. - PMC - PubMed
    11. O’Hara F, Blackmond DG, Baran PS. J Am Chem Soc. 2013;135:12122. - PMC - PubMed

    1. For select 2-pyridyl zinc reagents, see:

    2. Cornella J, Edwards JT, Qin T, Kawamura S, Wang J, Pan CM, Gianatassio R, Schmidt M, Eastgate MD, Baran PS. J Am Chem Soc. 2016;138:2174. - PMC - PubMed
    3. Colombe JR, Bernhardt S, Stathakis C, Buchwald SL, Knochel P. Org Lett. 2013;15:5754. - PMC - PubMed
    4. Luzung MR, Patel JS, Yin J. J Org Chem. 2010;75:8330. - PubMed

    5. For select 2-pyridyl boron reagents, see:

    6. Dick GR, Woerly EM, Burke MD. Angew Chem Int Ed. 2012;51:2667. - PMC - PubMed
    7. Sakashita S, Takisawa M, Sugai J, Ito H, Yamamoto Y. Org Lett. 2013;15:4308. - PubMed
    8. Billingsley KL, Buchwald SL. Angew Chem Int Ed. 2008;47:4695. - PMC - PubMed

    9. For 2-pyridyl tin reagents, see:

    10. Littke AF, Schawarz L, Fu GC. J Am Chem Soc. 2002;124:6343. - PubMed
    11. Bailey TR. Tetrahedron Lett. 1986;27:4407.

    12. For 2-pyridyl aluminum reagents, see:

    13. Chen X, Zhou L, Li Y, Xie T, Zhou S. J Org Chem. 2014;79:230. - PubMed

    1. For a select coupling reaction, see:

    2. Llaveria J, Leonori D, Aggarwal VK. J Am Chem Soc. 2015;137:10958. - PubMed

    1. For select Negishi and Kumada reactions, see:

    2. Malhotra S, Seng PS, Koenig SG, Deese AJ, Ford KA. Org Lett. 2013;15:3698. - PubMed
    3. Fürstner A, Leitner A. Angew Chem Int Ed. 2003;42:308. - PubMed
    4. Getmanenko YA, Tweig RJ. J Org Chem. 2008;73:830. - PubMed

    5. For cross-electrophile reactions, see:

    6. Everson DA, Buonomo JA, Weix DJ. Synlett. 2014;25:233. - PMC - PubMed

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