Organic Letters
Letter
M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505. (h) Shu, X. Z.;
Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136,
5844. (h) Tasker, S. Z.; Jamison, T. F. J. Am. Chem. Soc. 2015, 137,
9531.
Scheme 6. Ni/Photoredox-Catalyzed Cross-Coupling
Alkenyl Chlorides with Alkyl Bis(catecholato)silicates
a
(4) Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.;
Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896.
(5) Karakaya, I.; Primer, D. N.; Molander, G. A. Org. Lett. 2015, 17,
3294.
(6) El Khatib, M.; Serafim, R. A. M.; Molander, G. A. Angew. Chem.,
Int. Ed. 2016, 55, 254.
(7) Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am.
Chem. Soc. 2015, 137, 2195.
(8) Molander, G. A. J. Org. Chem. 2015, 80, 7837.
(9) Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc.
2016, 138, 475.
(10) Corce, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier,
C.; Fensterbank, L. Angew. Chem., Int. Ed. 2015, 54, 11414.
(11) (a) Matsuoka, D.; Nishigaichi, Y. Chem. Lett. 2014, 43, 559.
(b) Matsuoka, D.; Nishigaichi, Y. Chem. Lett. 2015, 44, 163.
(12) Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem.
Soc. 2015, 137, 624.
a
R′ = R″ = Et or R′ = H, R″ = i-Pr; all yields are isolated yields after
purification.
(13) Nishigaichi, Y.; Suzuki, A.; Takuwa, A. Tetrahedron Lett. 2007,
48, 211.
(14) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev.
2013, 113, 5322.
chlorides. The developed method complements existing
protocols for alkenyl cross-coupling via dual catalysis and
enables access to several previously inaccessible fragments.
Additionally, the mild reaction conditions allow functional
group tolerance, and complete stereochemical fidelity is
exhibited.
(15) (a) Jutand, A.; Negri, S. Organometallics 2003, 22, 4229.
(b) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1977, 99, 2501.
(16) Note that the source of the irradiation (CFL, white or blue
LEDs) had no effect on the overall outcome of the reaction.
(17) For examples, see: (a) Noble, A.; MacMillan, D. W. C. J. Am.
Chem. Soc. 2014, 136, 11602. (b) Singh, K.; Staig, S. J.; Weaver, J. D. J.
Am. Chem. Soc. 2014, 136, 5275.
ASSOCIATED CONTENT
(18) Note that both diisopropylammonium and triethylammonium
counterions show no discernible difference in reactivity or yield.
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S
* Supporting Information
The Supporting Information is available free of charge on the
Experimental details and spectral data (PDF)
AUTHOR INFORMATION
Corresponding Author
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Author Contributions
†N.R.P. and C.B.K. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We thank Kingson Lin (University of Pennsylvania) for the
preparation of alkylsilicates. We thank NIGMS (RO1
GM113878) for financial support of this research.
REFERENCES
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