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Communication
a
(7) For a representative review, see: Corey, E. J. Angew. Chem., Int.
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Scheme 8. 1,4-Arylboration
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(b) Semba, K.; Ohtagaki, Y.; Nakao, Y. Org. Lett. 2016, 18, 3956.
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Wang, B.; Liao, J. Angew. Chem., Int. Ed. 2016, 55, 13854. (f) For a
1,1-arylboration, see: Nelson, H. M.; Williams, B. D.; Miro,
F. D. J. Am. Chem. Soc. 2015, 137, 3213.
́
J.; Toste,
(10) For Cu-catalyzed protoboration of 1,3-dienes, see: (a) Semba,
K.; Shinomiya, M.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem. - Eur. J.
2013, 19, 7125. For Cu-catalyzed protoboration of other dienes, see:
(b) Sasaki, Y.; Zhong, C.; Sawamura, M.; Ito, H. J. Am. Chem. Soc.
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(11) (a) Smith, K. B.; Logan, K. M.; You, W.; Brown, M. K. Chem. -
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(13) Jia, T.; Cao, P.; Wang, B.; Lou, Y.; Yin, X.; Wang, M.; Liao, J. J.
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(14) For related Pd/Cu-catalyzed hydroarylation reactions, see:
(a) Semba, K.; Ariyama, K.; Zheng, H.; Kameyama, R.; Sakaki, S.;
Nakao, Y. Angew. Chem. 2016, 128, 6383. (b) Friis, S. D.; Pirnot, M.
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(15) Smith, K. B.; Brown, M. K. J. Am. Chem. Soc. 2017, 139, 7721.
(16) For a recent study, see: Russo, V.; Herron, J. R.; Ball, Z. T. Org.
Lett. 2010, 12, 220.
a
Yield determined by 1H NMR analysis of the crude reaction mixture
after oxidation with an internal standard, represents the average of two
or more experiments. All reactions carried out on a 0.3 mmol scale.
b
The starting diene was a mixture of alkene isomers (2:1−1:5:1 E:Z).
ASSOCIATED CONTENT
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S
* Supporting Information
The Supporting Information is available free of charge on the
Crystallographic data (PDB)
Experimental procedures, analytical data for all com-
Crystallographic data (CIF)
(17) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35.
(18) Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4,
916.
(19) See the Supporting Infromation for details.
(20) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000,
39, 4153.
AUTHOR INFORMATION
Corresponding Author
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(21) The failure of PhOTf to work with Pd-PAd2n-Bu is likely due to
the instability/poor reactivity of the generated Ph(OTf)PdPAd2n-Bu
complex under the reaction conditions. See the SI for details.
(22) Park, J.; McQuade, D. Synthesis 2012, 44, 1485.
(23) For enantioselective protoboration of cyclic dienes, see: Sasaki,
Y.; Zhong, C.; Sawamura, M.; Ito, H. J. Am. Chem. Soc. 2010, 132,
1226.
(24) Yang, C.-T.; Zhang, Z.-Q.; Liu, Y.-C.; Liu, L. Angew. Chem., Int.
Ed. 2011, 50, 3904.
(25) Torraca, K. E.; Kuwabe, S.-I.; Buchwald, S. L. J. Am. Chem. Soc.
2000, 122, 12907.
(26) Sonawane, R. P.; Jheengut, V.; Rabalakos, C.; Larouche-
Gauthier, R.; Scott, H. K.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011,
50, 3760.
ORCID
M. Kevin Brown: 0000-0002-4993-0917
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank Indiana University and the NIH (5R01GM114443)
for generous financial support.
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REFERENCES
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DOI: 10.1021/jacs.7b05477
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX