Organic Letters
Letter
(10) (a) Sen, M.; Emayavaramban, B.; Barsu, N.; Premkumar, J. R.;
Sundararaju, B. ACS Catal. 2016, 6, 2792−2796. (b) Barsu, N.; Sen,
M.; Sundararaju, B. Chem. Commun. 2016, 52, 1338−1341. (c) Barsu,
N.; Kalsi, D.; Sundararaju, B. Chem. - Eur. J. 2015, 21, 9364−9368.
(d) Sen, M.; Kalsi, D.; Sundararaju, B. Chem. - Eur. J. 2015, 21,
15529−15533. (e) Kalsi, D.; Sundararaju, B. Org. Lett. 2015, 17,
6118−6121.
AUTHOR INFORMATION
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Corresponding Author
Notes
The authors declare no competing financial interest.
(11) (a) Muralirajan, K.; Kuppusamy, R.; Prakash, S.; Cheng, C.-H.
Adv. Synth. Catal. 2016, 358, 774−783. (b) Kong, L.; Yu, S.; Zhou, X.;
Li, X. Org. Lett. 2016, 18, 588−591. (c) Sivakumar, G.; Vijeta, A.;
Jeganmohan, M. Chem. - Eur. J. 2016, 22, 5899−5903. (d) Lade, M.
D.; Pawar, A. B. Org. Chem. Front. 2016, 3, 836. (e) Boerth, J. A.;
ACKNOWLEDGMENTS
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Financial support provided by SERB (EMR/2016/000136) to
carryout this research is gratefully acknowledged. D.K. and N.B.
thank IITK and CSIR for their fellowships.
́ ́
(12) (a) Yu, D.-G.; Gensch, T.; de Azambuja, F.; Vasquez-Cespedes,
REFERENCES
■
S.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17722. Also see:
(b) Moselage, M.; Sauermann, N.; Koeller, J.; Liu, W.; Gelman, D.
Synlett 2015, 26, 1596−1600. Also see with Ru(II): Kumar, G. S.;
Kapur, M. Org. Lett. 2016, 18, 1112.
(1) Li, J. J. C−H Bond Activation in Organic Synthesis; CRC Press,
2015; pp 1−327.
(2) Dixneuf, P. H.; Doucet, H. C−H Bond Activation and Catalytic
Functionalization I; Springer, 2016; pp 1−76.
(13) (a) Bunno, Y.; Murakami, N.; Suzuki, Y.; Kanai, M.; Matsunaga,
(3) Selected recent reviews on C−H bond functionalization:
(a) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007. (b) Ye, B.;
Cramer, N. Acc. Chem. Res. 2015, 48, 1308. (c) Patureau, F. W.;
Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31−41.
(d) Davies, H. M. L.; Du Bois, J.; Yu, J.-Q. Chem. Soc. Rev. 2011, 40,
1855−1856. (e) Satoh, T.; Miura, M. Chem. - Eur. J. 2010, 16, 11212−
11222. (f) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev.
2010, 110, 624−655.
́ ́
S. Org. Lett. 2016, 18, 2216−2219. (b) Gensch, T.; Vasquez-Cespedes,
S.; Yu, D. − G.; Glorius, F. Org. Lett. 2015, 17, 3714−3717. (c) Suzuki,
Y.; Sun, B.; Sakata, K.; Yoshino, T.; Matsunaga, S.; Kanai, M. Angew.
Chem., Int. Ed. 2015, 54, 9944−9947. (d) Sun, B.; Yoshino, T.;
Matsunaga, S.; Kanai, M. Chem. Commun. 2015, 51, 4659−4661.
(14) Under oxidative conditions using Cp*Rh(III) favors β-hydride
elimination, see: (a) Shi, Z.; Boultadakis-Arapinis, M.; Glorius, F.
Chem. Commun. 2013, 49, 6489−6491. (b) Huang, L.; Wang, Q.; Qi,
J.; Wu, X.; Huang, K.; Jiang, H. Chem. Sci. 2013, 4, 2665−2669.
(c) Han, S. H.; Choi, M.; Jeong, T.; Sharma, S.; Mishra, N. K.; Park, J.;
Oh, J. S.; Kim, W. J.; Lee, J. S.; Kim, I. S. J. Org. Chem. 2015, 80,
11092−11099.
(4) Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew.
Chem., Int. Ed. 2013, 52, 2207−2211.
(5) Selected examples on Cp*Co(III)-catalyzed C−H bond
functionalization using pyridine or its analogues as directing group:
(a) Kim, J. H.; Greßies, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55,
5577−5581. (b) Barsu, N.; Atiur Rahman, Md.; Sen, M.; Sundararaju,
B. Chem. - Eur. J. 2016, 22, 9135. (c) Prakash, S.; Muralirajan, K.;
Cheng, C. − H. Angew. Chem., Int. Ed. 2016, 55, 1844. (d) Li, J.;
Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 3635−3638. (e) Li, J.;
Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 8551−8554.
(15) (a) Okamoto, T.; Kobayashi, T.; Yoshida, S. Med. Chem. 2007,
3, 35−44. (b) Bilel, H.; Hamdi, N.; Zagrouba, F.; Fischmeister, C.;
Bruneau, C. Catal. Sci. Technol. 2014, 4, 2064−2071.
(17) Dai, H.; Yu, C.; Wang, Z.; Yan, H.; Lu, C. Org. Lett. 2016, 18,
3410.
(18) See also a similar transformation with Ag(I): Chen, Z.; Yu, X.;
Su, M.; Yang, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 2702.
́
(f) Sauermann, N.; Gonzalez, M.; Ackermann, L. Org. Lett. 2015,
17, 5316−5319. (g) Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C.
A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508−4511. (h) Patel,
P.; Chang, S. ACS Catal. 2015, 5, 853−858. (i) Pawar, A. B.; Chang, S.
Org. Lett. 2015, 17, 660−663. (j) Liang, Y.; Liang, Y. − F.; Tang, C.;
Yuan, Y.; Jiao, N. Chem. - Eur. J. 2015, 21, 16395−16399. (k) Hummel,
J. R.; Ellman, J. A. J. Am. Chem. Soc. 2015, 137, 490−498. (l) Hummel,
J. R.; Ellman, J. A. Org. Lett. 2015, 17, 2400−2403. (m) Ozkal, E.;
Cacherat, B.; Morandi, B. ACS Catal. 2015, 5, 6458−6462. (n) Liu, X.
− G.; Zhang, S. − S.; Wu, J. − Q.; Li, Q.; Wang, H. Tetrahedron Lett.
2015, 56, 4093−4095. (o) Zhang, Z. − Z.; Liu, B.; Wang, C. − Y.; Shi,
B. − F. Org. Lett. 2015, 17, 4094−4097. (p) Sun, B.; Yoshino, T.;
Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 1491−1495.
(q) Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53,
10209−10212.
(6) (a) Lerchen, A.; Vas
Int. Ed. 2016, 55, 3208−3211. (b) Kim, J. H.; Greßies, S.; Glorius, F.
Angew. Chem., Int. Ed. 2016, 55, 5577−5581. (c) Lu, Q.; Vasquez-
Cespedes, S.; Gensch, T.; Glorius, F. ACS Catal. 2016, 6, 2352−2356.
́ ́
quez-Cespedes, S.; Glorius, F. Angew. Chem.,
́
́
(7) (a) Park, J.; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 14103−
14107. (b) Figg, T. M.; Park, S.; Park, J.; Chang, S.; Musav, D. G.
Organometallics 2014, 33, 4076−4085.
(8) (a) Sun, B.; Yoshino, T.; Kanai, M.; Matsunaga, S. Angew. Chem.,
Int. Ed. 2015, 54, 12968−12972. (b) Suzuki, Y.; Sun, B.; Yoshino, T.;
Matsunaga, S.; Kanai, M. Tetrahedron 2015, 71, 4552−4556.
(c) Ikemoto, H.; Yoshino, T.; Sakata, K.; Matsunaga, S.; Kanai, M. J.
Am. Chem. Soc. 2014, 136, 5424−5431.
́
(9) (a) Wang, H.; Moselage, M.; Gonzalez, M. J.; Ackermann, L. ACS
Catal. 2016, 6, 2705−2709. (b) Li, J.; Tang, M.; Zang, L.; Zhang, L.;
Zhang, Z.; Ackermann, L. Org. Lett. 2016, 18, 2742−2745. (c) Wang,
H.; Koeller, J.; Liu, W.; Ackermann, L. Chem. - Eur. J. 2015, 21,
15525−15528.
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