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. 2016 Sep 2;18(17):4440-3.
doi: 10.1021/acs.orglett.6b02323. Epub 2016 Aug 18.

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

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

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

Sébastien Laulhé et al. Org Lett. .

Abstract

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Alkylpyridine motifs are critical. Glc = d-glucose.
Scheme 1
Scheme 1. Selective and Serial Reactions
Scheme 2
Scheme 2. Serial Cross-Coupling Transformations
See this image and copyright information in PMC

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References

    1. Liu J.; Nakamura S.; Matsuda H.; Yoshikawa M. Tetrahedron Lett. 2013, 54, 32–34. 10.1016/j.tetlet.2012.10.052. - DOI
    2. Schinz H.; Ruzicka L.; Geyer U.; Prelog V. Helv. Chim. Acta 1946, 29, 1524–1528.
    3. Zhang Y.-H.; Shi B.-F.; Yu J.-Q. J. Am. Chem. Soc. 2009, 131, 5072–5074. 10.1021/ja900327e. - DOI - PMC - PubMed
    4. Davis J. M.; Truong A.; Hamilton A. D. Org. Lett. 2005, 7, 5405–5408. 10.1021/ol0521228. - DOI - PubMed
    1. Goetz A. E.; Garg N. K. Nat. Chem. 2013, 5, 54–60. 10.1038/nchem.1504. - DOI - PMC - PubMed

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

    2. Jeffrey J. L.; Sarpong R. Org. Lett. 2012, 14, 5400–5403. 10.1021/ol3024117. - DOI - PMC - PubMed
    3. Chen Q.; León T.; Knochel P. Angew. Chem., Int. Ed. 2014, 53, 8746–8750. 10.1002/anie.201400750. - DOI - PubMed
    4. Hyodo I.; Tobisu M.; Chatani N. Chem. - Asian J. 2012, 7, 1357–1365. 10.1002/asia.201100971. - DOI - PubMed
    1. Lewis J. C.; Bergman R. G.; Ellman J. A. J. Am. Chem. Soc. 2007, 129, 5332–5333. 10.1021/ja070388z. - DOI - PMC - PubMed
    2. Nakao Y.; Yamada Y.; Kashihara N.; Hiyama T. J. Am. Chem. Soc. 2010, 132, 13666–13668. 10.1021/ja106514b. - DOI - PubMed

    1. For select Minisci-type pathways, see:

    2. Jin J.; MacMillan D. W. C. Nature 2015, 525, 87–90. 10.1038/nature14885. - DOI - PMC - PubMed
    3. Gianatassio R.; Kawamura S.; Eprile C. L.; Foo K.; Ge J.; Burns A. C.; Collins M. R.; Baran P. S. Angew. Chem., Int. Ed. 2014, 53, 9851–9855. 10.1002/anie.201406622. - DOI - PMC - PubMed
    4. O’Hara F.; Blackmond D. G.; Baran P. S. J. Am. Chem. Soc. 2013, 135, 12122–12134. 10.1021/ja406223k. - DOI - PMC - PubMed

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