Organic Letters
Letter
IV,4f,18 which is arylated by arene to afford intermediate V, and
then the following reductive elimination resulted in product
formation and Pd catalyst regeneration.
In summary, the transient directing strategy was successfully
utilized in the direct oxidative dehydrogenative arylation of
aldehydes with arenes for the first time. Featured by mild
reaction conditions, good functional group compatibility, and
great regioselectivity, the method should find broad applica-
tions in new medicine and material development and discovery
processes. Detailed mechanism and application studies are
currently ongoing in our laboratory.
(4) (a) Brasche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett.
2008, 10, 2207. (b) Yeung, C. S.; Zhao, X.; Borduas, N.; Dong, V. M.
Chem. Sci. 2010, 1, 331. (c) Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem.
Soc. 2011, 133, 13864. (d) Yang, F.; Song, F.; Li, W.; Lan, J.; You, J.
RSC Adv. 2013, 3, 9649. (e) Yang, F.; Rauch, K.; Kettelhoit, K.;
Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 11285. (f) Yang, Z.;
Qiu, F.-C.; Gao, J.; Li, Z.-W.; Guan, B.-T. Org. Lett. 2015, 17, 4316.
(5) For the reaction of the C(sp2)−H bond: (a) Jun, C.-H.; Lee, H.;
Hong, J.-B. J. Org. Chem. 1997, 62, 1200. (b) Chen, X.-Y.; Ozturk, S.;
Sorensen, E. J. Org. Lett. 2017, 19, 6280. (c) Hu, W.; Zheng, Q.; Sun,
S.; Cheng, J. Chem. Commun. 2017, 53, 6263. (d) Xu, J.; Liu, Y.; Wang,
Y.; Li, Y.; Xu, X.; Jin, Z. Org. Lett. 2017, 19, 1562. (e) Yao, Q.-J.;
Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
(f) Xu, J.; Liu, Y.; Zhang, J.; Xu, X.; Jin, Z. Chem. Commun. 2018, 54,
689. (g) Li, F.; Zhou, Y.; Yang, H.; Liu, D.; Sun, B.; Zhang, F.-L. Org.
Lett. 2018, 20, 146. (h) Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.;
Huang, D.-Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, DOI: 10.1002/
ASSOCIATED CONTENT
■
S
* Supporting Information
The Supporting Information is available free of charge on the
(6) For the reaction of the C(sp3)−H bond: (a) Mo, F.; Dong, G.
Science 2014, 345, 68. (b) Wu, Y.; Chen, Y.-Q.; Liu, T.; Eastgate, M.
D.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 14554. (c) Liu, Y.; Ge, H.
Nat. Chem. 2016, 9, 26. (d) Xu, Y.; Young, M. C.; Wang, C.; Magness,
D. M.; Dong, G. Angew. Chem., Int. Ed. 2016, 55, 9084. (e) Xu, Y.;
Young, M. C.; Dong, G. J. Am. Chem. Soc. 2017, 139, 5716. (f) Zhu,
R.-Y.; Liu, L.-Y.; Yu, J.-Q. J. Am. Chem. Soc. 2017, 139, 12394. (g) Zhu,
R.-Y.; Liu, L.-Y.; Park, H. S.; Hong, K.; Wu, Y.; Senanayake, C. H.; Yu,
J.-Q. J. Am. Chem. Soc. 2017, 139, 16080. (h) Hong, K.; Park, H.; Yu,
J.-Q. ACS Catal. 2017, 7, 6938. (i) Yada, A.; Liao, W.; Sato, Y.;
Murakami, M. Angew. Chem., Int. Ed. 2017, 56, 1073.
(7) Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016,
351, 252.
(8) For benzylic arylation of o-tolualdehydes with iodobenzenes: Ma,
F.; Lei, M.; Hu, L. Org. Lett. 2016, 18, 2708.
(9) Yang, K.; Li, Q.; Liu, Y.; Li, G.; Ge, H. J. Am. Chem. Soc. 2016,
138, 12775.
Experimental procedures and spectral data (PDF)
Accession Codes
mentary crystallographic data for this paper. These data can be
contacting The Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
(10) Liu, X.-H.; Park, H.; Hu, J.-H.; Hu, Y.; Zhang, Q.-L.; Wang, B.-
L.; Sun, B.; Yeung, K.-S.; Zhang, F.-L.; Yu, J.-Q. J. Am. Chem. Soc.
2017, 139, 888.
(11) Chen, X.-Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 1140.
(12) St John-Campbell, S.; White, A. J. P.; Bull, J. A. Chem. Sci. 2017,
8, 4840.
Notes
The authors declare no competing financial interest.
(13) Zhang, X.; Zheng, H.; Li, J.; Xu, F.; Zhao, J.; Yan, H. J. Am.
Chem. Soc. 2017, 139, 14511.
ACKNOWLEDGMENTS
■
(14) McIntire, F. C. J. Am. Chem. Soc. 1947, 69, 1377.
(15) (a) Lu, W.; Yamaoka, Y.; Taniguchi, Y.; Kitamura, T.; Takaki,
K.; Fujiwara, Y. J. Organomet. Chem. 1999, 580, 290. (b) Chen, W.-L.;
Gao, Y.-R.; Mao, S.; Zhang, Y.-L.; Wang, Y.-F.; Wang, Y.-Q. Org. Lett.
2012, 14, 5920.
(16) (a) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F.
Angew. Chem., Int. Ed. 2012, 51, 10236. (b) Wencel-Delord, J.;
Nimphius, C.; Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2012,
51, 2247. (c) Wencel-Delord, J.; Nimphius, C.; Wang, H.; Glorius, F.
Angew. Chem., Int. Ed. 2012, 51, 13001.
We are grateful for financial support from the National Natural
Science Foundation of China (NSFC-21572178 and NSFC-
21702162), Natural Science Basic Research Plan in Shaanxi
Province of China (Program No. 2017JM2006), the Key
Science and Technology Innovation Team of Shaanxi Province
(2017KCT-37), and Scientific Research Program Funded by
Shaanxi Provincial Education Department (Program No.
17JK0788).
(17) Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118.
(18) (a) Karthikeyan, J.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011,
50, 9880. (b) Thirunavukkarasu, V. S.; Cheng, C.-H. Chem. - Eur. J.
2011, 17, 14723.
REFERENCES
■
(1) Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure, 6th ed.; Wiley-Interscience: New York,
2007.
(2) (a) Padala, K.; Jeganmohan, M. Org. Lett. 2012, 14, 1134. (b) Liu,
X.; Li, X.; Liu, H.; Guo, Q.; Lan, J.; Wang, R.; You, J. Org. Lett. 2015,
17, 2936. (c) Santhoshkumar, R.; Mannathan, S.; Cheng, C. H. J. Am.
Chem. Soc. 2015, 137, 16116.
(3) (a) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (b) Jun, C.-H.; Jo,
E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 2007, 1869. (c) Fristrup, P.;
Kreis, M.; Palmelund, A.; Norrby, P.-O.; Madsen, R. J. Am. Chem. Soc.
2008, 130, 5206. (d) Garralda, M. A. Dalton Trans. 2009, 3635.
(e) Willis, M. C. Chem. Rev. 2010, 110, 725. (f) Modak, A.; Deb, A.;
Patra, T.; Rana, S.; Maity, S.; Maiti, D. Chem. Commun. 2012, 48,
4253. (g) Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202.
(h) Murphy, S. K.; Dong, V. M. Chem. Commun. 2014, 50, 13645.
D
Org. Lett. XXXX, XXX, XXX−XXX