Chiral Phosphoric Acid Catalyzed Atroposelective C-H Amination of Arenes.
amination
atropisomerism
chiral phosphoric acid
heterocycles
organocatalysis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
20 Apr 2020
20 Apr 2020
Historique:
received:
13
01
2020
pubmed:
6
2
2020
medline:
6
2
2020
entrez:
5
2
2020
Statut:
ppublish
Résumé
N-arylcarbazole structures are important because of their prevalence in natural products and functional OLED materials. C-H amination of arenes has been widely recognized as the most efficient approach to access these structures. Conventional strategies involving transition-metal catalysts suffer from confined substrate generality and the requirement of exogenous oxidants. Organocatalytic enantioselective C-N chiral axis construction remains elusive. Presented here is the first organocatalytic strategy for the synthesis of novel axially chiral N-arylcarbazole frameworks by the assembly of azonaphthalenes and carbazoles. This reaction accommodates broad substrate scope and gives atropisomeric N-arylcarbazoles in good yields with excellent enantiocontrol. This approach not only offers an alternative to metal-catalyzed C-N cross-coupling, but also brings about opportunities for the exploitation of structurally diverse N-aryl atropisomers and OLED materials.
Identifiants
pubmed: 32017378
doi: 10.1002/anie.202000585
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6775-6779Subventions
Organisme : National Natural Science Foundation of China
ID : 21772081, 21825105
Organisme : Innovative Research Group Project of the National Natural Science Foundation of China
ID : 21702092
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
A. Ricci, Amino Group Chemistry: From Synthesis to the Life Sciences, Wiley-VCH, Weinheim, 2008;
D. A. Horton, G. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893-930;
S. Bhattacharya, P. Chaudhuri, Curr. Med. Chem. 2008, 15, 1762-1777;
D.-J. Liaw, K.-L. Wang, Y.-C. Huang, K.-R. Lee, J.-Y. Lai, C.-S. Ha, Prog. Polym. Sci. 2012, 37, 907-974.
P. Strohriegl, J. V. Grazulevicius, Adv. Mater. 2002, 14, 1439-1452;
S. Sebastian, D. Kondakov, B. Lüssem, K. Leo, Chem. Rev. 2015, 115, 8449-8503;
S. Hirata, Y. Sakai, K. Masui, H. Tanaka, S.-Y. Lee, H. Nomura, N. Nakamura, M. Yasumatsu, H. Nakanotani, Q. Zhang, K. Shizu, H. Miyazaki, C. Adachi, Nat. Mater. 2015, 14, 330-336;
S. Feuillastre, M. Pauton, L. Gao, A. Desmarchelier, A. J. Riives, D. Prim, D. Tondelier, B. Geffroy, G. Muller, G. Clavier, G. Pieters, J. Am. Chem. Soc. 2016, 138, 3990-3993;
Z. Yang, Z. Mao, Z. Xie, Y. Zhang, S. Liu, J. Zhao, J. Xu, Z. Chi, M. P. Aldred, Chem. Soc. Rev. 2017, 46, 915-1016;
B. Wex, B. R. Kaafarani, J. Mater. Chem. C 2017, 5, 8622-8653;
X. Cao, D. Zhang, S. Zhang, Y. Tao, W. Huang, J. Mater. Chem. C 2017, 5, 7699-7714.
I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337-2364;
G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054-3131;
J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534-1544;
J. Bariwal, E. Van der Eycken, Chem. Soc. Rev. 2013, 42, 9283-9303;
C. Sambiagio, S. P. Marsden, A. J. Blacker, P. C. McGowan, Chem. Soc. Rev. 2014, 43, 3525-3550;
P. Ruiz-Castillo, S. L. Buchwald, Chem. Rev. 2016, 116, 12564-12649.
H.-J. Kim, J. Kim, S.-H. Cho, S. Chang, J. Am. Chem. Soc. 2011, 133, 16382-16385;
A. A. Kantak, S. Potavathri, R. A. Barham, K. M. Romano, B. DeBoef, J. Am. Chem. Soc. 2011, 133, 19960-19965.
L. D. Tran, J. Roane, O. Daugulis, Angew. Chem. Int. Ed. 2013, 52, 6043-6046;
Angew. Chem. 2013, 125, 6159-6162;
R. Shrestha, P. Mukherjee, Y. Tan, Z. C. Litman, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 8480-8483;
M. Shang, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 3354-3357;
H. Xu, X. Qiao, S. Yang, Z. Shen, J. Org. Chem. 2014, 79, 4414-4422;
Q. Yan, Z. Chen, W. Yu, H. Yin, Z. Liu, Y. Zhang, Org. Lett. 2015, 17, 2482-2485;
L.-B. Zhang, S.-K. Zhang, D. Wei, X. Zhu, X.-Q. Hao, J.-H. Su, J.-L. Niu, M.-P. Song, Org. Lett. 2016, 18, 1318-1321;
M. P. Paudyal, A. M. Adebesin, S. R. Burt, D. H. Ess, Z. Ma, L. Kürti, J. R. Falck, Science 2016, 353, 1144-1147.
N. A. Romero, K. A. Margrey, N. E. Tay, D. A. Nicewicz, Science 2015, 349, 1326-1330;
K. A. Margrey, J. B. McManus, S. Bonazzi, F. Zecri, D. A. Nicewicz, J. Am. Chem. Soc. 2017, 139, 11288-11299;
L. Niu, H. Yi, S. Wang, T. Liu, J. Liu, A. Lei, Nat. Commun. 2017, 8, 14226;
A. Ruffoni, F. Juliá, T. D. Svejstrup, A. J. McMillan, J. J. Douglas, D. Leonori, Nat. Chem. 2019, 11, 426-433.
N. Sauermann, R. Mei, L. Ackermann, Angew. Chem. Int. Ed. 2018, 57, 5090-5094;
Angew. Chem. 2018, 130, 5184-5188;
Q.-L. Yang, X.-Y. Wang, J.-Y. Lu, L.-P. Zhang, P. Fang, T.-S. Mei, J. Am. Chem. Soc. 2018, 140, 11487-11494;
X. Gao, P. Wang, L. Zeng, S. Tang, A. Lei, J. Am. Chem. Soc. 2018, 140, 4195-4199;
P. Feng, G. Ma, X. Chen, X. Wu, L. Lin, P. Liu, T. Chen, Angew. Chem. Int. Ed. 2019, 58, 8400-8404;
Angew. Chem. 2019, 131, 8488-8492;
J.-H. Wang, T. Lei, X.-L. Nan, H.-L. Wu, X.-B. Li, B. Chen, C.-H. Tung, L.-Z. Wu, Org. Lett. 2019, 21, 5581-5585;
L. Zhang, L. Liardet, J. Luo, D. Ren, M. Grätzel, X. Hu, Nat. Catal. 2019, 2, 366-373.
L.-W. Qi, J.-H. Mao, J. Zhang, B. Tan, Nat. Chem. 2018, 10, 58-64;
L.-W. Qi, S. Li, S.-H. Xiang, J. Wang, B. Tan, Nat. Catal. 2019, 2, 314-323.
T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
Angew. Chem. 2004, 116, 1592-1594;
D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047-9153.
For typical reviews, see:
M. C. Kozlowski, B. J. Morgan, E. C. Linton, Chem. Soc. Rev. 2009, 38, 3193-3207;
E. Kumarasamy, R. Raghunathan, M. P. Sibi, J. Sivaguru, Chem. Rev. 2015, 115, 11239-11300;
J. Wencel-Delord, A. Panossian, F. R. Leroux, F. Colobert, Chem. Soc. Rev. 2015, 44, 3418-3430;
D. Bonne, J. Rodriguez, Eur. J. Org. Chem. 2018, 2417-2431;
D. Bonne, J. Rodriguez, Chem. Commun. 2017, 53, 12385-12393; For selected examples:
J. L. Gustafson, D. Lim, S. J. Miller, Science 2010, 328, 1251-1255;
K. Mori, Y. Ichikawa, M. Kobayashi, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 3964-3970;
K. T. Barrett, A. J. Metrano, P. R. Rablen, S. J. Miller, Nature 2014, 509, 71-75;
J.-Z. Wang, J. Zhou, C. Xu, H. Sun, L. Kürti, Q.-L. Xu, J. Am. Chem. Soc. 2016, 138, 5202-5205;
O. Quinonero, M. Jean, N. Vanthuyne, C. Roussel, D. Bonne, T. Constantieux, C. Bressy, X. Bugaut, J. Rodriguez, Angew. Chem. Int. Ed. 2016, 55, 1401-1405;
Angew. Chem. 2016, 128, 1423-1427;
V. S. Raut, M. Jean, N. Vanthuyne, C. Roussel, T. Constantieux, C. Bressy, X. Bugaut, D. Bonne, J. Rodriguez, J. Am. Chem. Soc. 2017, 139, 2140-2143;
H.-H. Zhang, C.-S. Wang, C. Li, G.-J. Mei, Y. Li, F. Shi, Angew. Chem. Int. Ed. 2017, 56, 116-121;
Angew. Chem. 2017, 129, 122-127;
J. D. Jolliffe, R. J. Armstrong, M. D. Smith, Nat. Chem. 2017, 9, 558-562;
K. Zhao, L. Duan, S. Xu, J. Jiang, Y. Fu, Z. Gu, Chem 2018, 4, 599-612;
V. Hornillos, J. A. Carmona, A. Ros, J. Iglesias-Sigüenza, J. López-Serrano, R. Fernández, J. M. Lassaletta, Angew. Chem. Int. Ed. 2018, 57, 3777-3781;
Angew. Chem. 2018, 130, 3839-3843;
S. Jia, Z. Chen, N. Zhang, Y. Tan, Y. Liu, J. Deng, H. Yan, J. Am. Chem. Soc. 2018, 140, 7056-7060;
S.-C. Zheng, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2019, 58, 1494-1498;
Angew. Chem. 2019, 131, 1508-1512;
J. Luo, T. Zhang, L. Wang, G. Liao, Q.-J. Yao, Y.-J. Wu, B.-B. Zhan, Y. Lan, X.-F. Lin, B.-F. Shi, Angew. Chem. Int. Ed. 2019, 58, 6708-6712;
Angew. Chem. 2019, 131, 6780-6784;
G. Liao, H.-M. Chen, Y.-N. Xia, B. Li, Q.-J. Yao, B.-F. Shi, Angew. Chem. Int. Ed. 2019, 58, 11464-11468;
Angew. Chem. 2019, 131, 11586-11590;
F. Jiang, K.-W. Chen, P. Wu, Y.-C. Zhang, Y. Jiao, F. Shi, Angew. Chem. Int. Ed. 2019, 58, 15104-15110;
Angew. Chem. 2019, 131, 15248-15254;
R. Deng, J. Xi, Q. Li, Z. Gu, Chem 2019, 5, 1834-1846;
D. Shen, Y. Xu, S.-L. Shi, J. Am. Chem. Soc. 2019, 141, 14938-14945;
R. M. Witzig, V. C. Fäseke, D. Häussinger, C. Sparr, Nat. Catal. 2019, 2, 925-930.
Y.-B. Wang, B. Tan, Acc. Chem. Res. 2018, 51, 534-547;
Y.-B. Wang, P. Yu, Z.-P. Zhou, J. Zhang, J. Wang, S.-H. Luo, Q.-S. Gu, K. N. Houk, B. Tan, Nat. Catal. 2019, 2, 504-513.
M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. Int. Ed. 2004, 43, 550-556;
Angew. Chem. 2004, 116, 560-566;
M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed. 2009, 48, 9608-9644;
Angew. Chem. 2009, 121, 9786-9824;
M. Zeng, S.-L. You, Synlett 2010, 1289-1301.
Y. Zhang, Y.-K. Liu, T.-R. Kang, Z.-K. Hu, Y.-C. Chen, J. Am. Chem. Soc. 2008, 130, 2456-2457.
L. Zhang, S.-H. Xiang, J. Wang, J. Xiao, J.-Q. Wang, B. Tan, Nat. Commun. 2019, 10, 566.
X. Bao, J. Rodriguez, D. Bonne, Chem. Sci. 2020, 11, 403-408.
J. P. Vigneron, M. Dhaenens, A. Horeau, Tetrahedron 1973, 29, 1055-1059;
A. M. Harned, Tetrahedron 2018, 74, 3797-3841.
CCDC 1963374 (8) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.