Organic Letters
Letter
(4) (a) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365−1377.
(b) Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918−4931.
(c) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427−2440. (d) Murphy,
G. K.; Stewart, C.; West, F. G. Tetrahedron 2013, 69, 2667−2686.
(e) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236−247.
(f) Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024−10030. (g) Xing, D.;
Hu, W. Tetrahedron Lett. 2014, 55, 777−783. (h) Burtoloso, A. C. B.;
Santiago, J. V.; Bernardim, B.; Talero, A. G. Curr. Org. Synth. 2015, 12,
650−659. (i)Hu,F.;Xia,Y.;Ma, C.;Zhang,Y.;Wang, J. Chem. Commun.
2015, 51, 7986−7995. (j) Qian, D.; Zhang, J. Chem. Soc. Rev. 2015, 44,
677−698. (k) Wang, B.; Qiu, D.; Zhang, Y.; Wang, J. Beilstein J. Org.
Chem. 2016, 12, 796−804. (l) Guttenberger, N.; Breinbauer, R.
Tetrahedron 2017, 73, 6815−6829. (m) Keipour, H.; Carreras, V.;
Ollevier, T. Org. Biomol. Chem. 2017, 15, 5441−5456.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Author Contributions
The manuscript was written through contributions of all authors.
Notes
The authors declare no competing financial interest.
(5) (a) Candeias, N. R.; Afonso, C. A. M. Curr. Org. Chem. 2009, 13,
ACKNOWLEDGMENTS
■
́
763−787. (b) Zhang, Y.; Burdzinski, G.; Kubicki, J.; Platz, M. S. J. Am.
S.B.N. thanks UGC, New Delhi for the Ph.D fellowship. We
thankSAIFdivisionofCSIR-CDRIfortheanalyticalsupport.We
gratefully acknowledge the X-ray diffraction facility of Indian
InstituteofTechnology, KanpurforX-raydatacollectionof3zb′.
We are thankful to Dr. Iti Gupta, Department of Chemistry,
Indian Institute of Technology, Gandhi Nagar for recording CV
data of 1a. We also acknowledge Department of Science &
Technology(DST), New Delhi for the financial support (Project
ref. No.: EMR/2016/006975). CDRI Communication No.
9867.
Chem. Soc. 2009, 131, 9646−9647. (c) Yang, Z.; Xu, J. Tetrahedron Lett.
2012,53,786−789. (d)Navarro,R.;Perrino,M. P.;Prucker,O.;Ruhe,J.
̈
Langmuir 2013, 29, 10932−10939. (e) Cui, G.; Thiel, W. Angew. Chem.,
Int. Ed. 2013, 52, 433−436. (f) Willumstad, T. P.; Haze, O.; Mak, X. O.;
Lam, T. Y.;Wang, Y.-P.; Danheiser, R. L. J. Org. Chem. 2013, 78, 11450−
11469. (g) Galkina, O. S.; Rodina, L. L. Russ. Chem. Rev. 2016, 85, 537−
555. (h)Rodina, L. L.;Galkina, O. S.;Maas, G.;Platz, M. S.;Nikolaev, V.
́
A. Asian J. Org. Chem. 2016, 5, 691−698. (i) Rybicka-Jasinska, K.; Shan,
W.; Zawada, K.; Kadish, K. M.; Gryko, D. J. Am. Chem. Soc. 2016, 138,
15451−15458. (j) Rodina, L. L.; Baranovskii, V. I.; Galkina, O. S.;
Nikolaev, V. A.; Tonogina, N. L.; Povolotskiy, A. V. J. Org. Chem. 2017,
82, 11399−11405.(k)Talero, A. G.;Burtoloso, A. C. B. Synlett2017, 28,
1748−1752. (l)Forneris, C. C.;Wang, Y.-P.; Mamaliga, G.;Willumstad,
T.P.;Danheiser,R. L.Org.Lett. 2018,20,6318−6322.(m)Ciszewski, L.
REFERENCES
■
(1) (a) Nawrat, C. C.; Moody, C. J. Nat. Prod. Rep. 2011, 28, 1426−
1444. (b) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.;
McKervey, M. A. Chem. Rev. 2015, 115, 9981−10080. (c) Mix, K. A.;
Aronoff, M. R.; Raines, R. T. ACS Chem. Biol. 2016, 11, 3233−3244.
(d)Marinozzi,M.;Pertusati, F.;Serpi, M.Chem. Rev.2016,116,13991−
14055. (e) Mertens, L.; Koenigs, R. M. Org. Biomol. Chem. 2016, 14,
10547−10556. (f)Candeias, N. R.;Paterna, R.;Gois, P. M. P. Chem. Rev.
2016, 116, 2937−2981. (g) Cheng, Q.-Q.; Deng, Y.; Lankelma, M.;
Doyle, M. P. Chem. Soc. Rev. 2017, 46, 5425−5443. (h) Li, Y.-P.; Li, Z.-
Q.; Zhu, S.-F. Tetrahedron Lett. 2018, 59, 2307−2316. (i) Wang, J. Pure
Appl.Chem. 2018,90,617−623. (j)Dhameja,M.;Pandey,J. AsianJ. Org.
Chem. 2018, 7, 1502−1523. (k) Xiang, Y.; Wang, C.; Ding, Q.; Peng, Y.
Adv. Synth. Catal. 2019, 361, 919−944.
(2) (a) Zhao, Y.; Wang, J. Synlett 2005, 2005, 2886−2892.
(b) Friedman, R.; Caflisch, A. ChemMedChem 2009, 4, 1317−1326.
(c) Zhang, Y.; Wang, J. Chem. Commun. 2009, 45, 5350−5361.
(d) Hashimoto, T.; Maruoka, K. Bull. Chem. Soc. Jpn. 2013, 86, 1217−
1230. (e) An, S. S.; Chi, K.-W.; Kim, I.; Song, Y. H.; Singh, N.; Jeong, Y.
J.; Kwon, J. E.; Kim, H.; Cho, Y.; Kang, S. C. Int. J. Nanomed. 2015, 10,
143−153. (f) Guedouar, H.; Aloui, F.; Beltifa, A.; Mansour, H. B.;
Hassine, B. B. C. R. C. R. Chim. 2017, 20, 841−849. (g) Baiju, T. V.;
Namboothiri, I. N. N. Chem. Rec. 2017, 17, 939−955.
́
W.; Rybicka-Jasinska, K.; Gryko, D. Org. Biomol. Chem. 2019, 17, 432−
448.
(6) (a) Xiao, T.; Li, L.; Lin, G.; Mao, Z.-W.; Zhou, L. Org. Lett. 2014,
16, 4232−4235. (b) Xia, X.-D.; Ren, Y.-L.; Chen, J.-R.; Yu, X.-L.; Lu, L.-
Q.; Zou, Y.-Q.; Wan, J.; Xiao, W.-J. Chem. - Asian J. 2015, 10, 124−128.
(c) Liu, Y.; Dong, X.; Deng, G.; Zhou, L. Sci. China: Chem. 2016, 59,
́
199−202. (d) Rybicka-Jasinska, K.; Ciszewski, Ł. W.; Gryko, D. Adv.
Synth. Catal. 2016, 358, 1671−1678. (e) Pramanik, M. M. D.; Nagode,
S. B.; Kant, R.; Rastogi, N. Org. Biomol. Chem. 2017, 15, 7369−7373.
(f) Ma, M.; Hao, W.; Ma, L.; Zheng, Y.; Lian, P.; Wan, X. Org. Lett. 2018,
́
20, 5799−5802. (g) Rybicka- Jasinska, K.; Orłowska, K.; Karczewski,
M.; Zawada, K.; Gryko, D. Eur. J. Org. Chem. 2018, 2018, 6634−6642.
(7) Wang, Z.; Herraiz, A. G.; del Hoyo, A. M.; Suero, M. G. Nature
2018, 554, 86−91.
(8) (a) Vaske, Y. S. M.; Mahoney, M. E.; Konopelski, J. P.; Rogow, D.
L.; McDonald, W. J. J. Am. Chem. Soc. 2010, 132, 11379−11385.
(b) Bernardim, B.; Hardman-Baldwin, A. M.; Burtoloso, A. C. B. RSC
Adv. 2015, 5, 13311−13314.
(9) Jurberg, I. D.; Davies, H. M. L. Chem. Sci. 2018, 9, 5112−5118.
(10) (a) Zhang, X.; Du, C.; Zhang, H.; Li, X.-C.; Wang, Y. L.; Niu, J.-L.;
Song, M.-P. Synthesis 2019, 51, 889−898. (b) Hommelsheim, R.; Guo,
Y.; Yang, Z.; Empel, C.; Koenigs, R. M. Angew. Chem., Int. Ed. 2019, 58,
1203−1207.
(3) (a) Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48,
10162−10173. (b) Bera, K.; Sarkar, S.; Jalal, S.; Jana, U. J. Org. Chem.
2012, 77, 8780−8786. (c) Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013,
42,4918−4931.(d)Patel,D.G.;Walton,I.M.;Cox,J.M.;Gleason,C.J.;
Butzer, D. R.; Benedict, J. B. Chem. Commun. 2014, 50, 2653−2656.
(e) Li, M.; An, C.; Marszalek, T.; Guo, X.; Long, Y.-Z.; Yin, H.; Gu, C.;
(11) Xiao, T.; Mei, M.; He, Y.; Zhou, L. Chem. Commun. 2018, 54,
8865−8868.
(12) Bethell, D.; Parker, V. D. Acc. Chem. Res. 1988, 21, 400−407.
(13) He, Y.; Chen, H.; Li, L.; Huang, J.; Xiao, T.; Anand, D.; Zhou, L. J.
Photochem. Photobiol., A 2018, 355, 220−225.
Baumgarten, M.; Pisula, W.; Mullen, K. Chem. Mater. 2015, 27, 2218−
̈
(14) (a) Ravelli, D.; Fagnoni, M. ChemCatChem 2012, 4, 169−171.
2223. (f) Bera, K.; Sarkar, S.; Jana, U. Tetrahedron Lett. 2015, 56, 312−
(b) Hari, D. P.; Kunig, B. Chem. Commun. 2014, 50, 6688−6699.
̈
315. (g) Caballero, A.; Díaz-Requejo, M. M.; Fructos, M. R.; Olmos, A.;
(c) Majek, M.; Filace, F.; Wangelin, A. J. Beilstein J. Org. Chem. 2014, 10,
981−989.
́
Urbano, J.; Perez, P. J. Dalton Trans. 2015, 44, 20295−20307.
́
(h) Fructos, M. R.; Díaz- Requejo, M. M.; Perez, P. J. Chem. Commun.
(15) Jung, J.; Kim, J.; Park, G.; You, Y.; Chob, E. J. Adv. Synth. Catal.
2016, 358, 74−80.
2016, 52, 7326−7335. (i) Torres, O.; Anna, P.-Q. Tetrahedron Lett.
2016, 57, 3881−3891. (j) Liu, L.; Zhang, J. Chem. Soc. Rev. 2016, 45,
506−516. (k) Kim, Y.-A.; Hwang, K-II.; Kang, M.; Kim, N.-K.; Jang, S.-
Y.; Kim, I.-B.; Kim, J.; Kim, D.-Y. Org. Electron. 2017, 44, 238−246.
(l) Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810−13889.
(m) Cheng, Q.-Q.; Yu, Y.; Yedoyan, J.; Doyle, M. P. ChemCatChem
2018, 10, 488−496.
(16) (a) Huang, W.; Cheng, X. Synlett 2017, 28, 148−158. (b) Gu, F.;
Huang, W.; Liu, X.; Chen, W.; Cheng, X. Adv. Synth. Catal. 2018, 360,
925−931. (c) Song, Z.-Y.; Zhang, C.-L.; Ye, S. Org. Biomol. Chem. 2019,
17, 181−185. (d) Ji, P.; Zhang, Y.; Wei, Y.; Huang, H.; Hu, W.;Mariano,
P. A.; Wang, W. Org. Lett. 2019, 21, 3086−3092.
E
Org. Lett. XXXX, XXX, XXX−XXX