Silver-Catalyzed Synthesis of Benzyl Ethers via Alkoxylation of Benzylic C(sp
alkoxylation
potassium persulfate
radicals
silver
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
17 Jul 2023
17 Jul 2023
Historique:
revised:
29
05
2023
received:
16
05
2023
medline:
31
5
2023
pubmed:
31
5
2023
entrez:
31
5
2023
Statut:
ppublish
Résumé
Alkoxylation of benzylic C(sp
Identifiants
pubmed: 37254654
doi: 10.1002/asia.202300425
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300425Subventions
Organisme : Top Youth Talent Fund of Zhengzhou University
Organisme : Startup Research Fund of Zhengzhou University
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318-5365;
G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054-3131;
D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41, 1450-1460;
F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 6954-6971;
S. Enthaler, A. Company, Chem. Soc. Rev. 2011, 40, 4912-4924;
P. J. Borpatra, B. Deka, M. L. Deb, P. K. Baruah, Org. Chem. Front. 2019, 6, 3445-3489;
S. Zhu, H. Li, Y. Li, Z. Huang, L. Chu, Org. Chem. Front. 2023, 10, 548-569.
N. A. Powell, E. H. Clay, D. D. Holsworth, J. W. Bryant, M. J. Ryan, M. Jalaie, J. J. Edmunds, Bioorg. Med. Chem. Lett. 2005, 15, 4713-4716;
Y.-L. Leu, C.-S. Chen, Y.-J. Wu, J.-W. Chern, J. Med. Chem. 2008, 51, 1740-1746;
S. D. Roughley, A. M. Jordan, J. Med. Chem. 2011, 54, 3451-3479;
K. Sapkota, E. Roh, E. Lee, E.-M. Ha, J.-H. Yang, E.-S. Lee, Y. Kwon, Y. Kim, Y. Na, Bioorg. Med. Chem. 2011, 19, 2168-2175;
D. A. Patrick, S. A. Bakunov, S. M. Bakunova, S. K. Jones, T. Wenzler, T. Barszcz, A. Kumar, D. W. Boykin, K. A. Werbovetz, R. Brun, R. R. Tidwell, Eur. J. Med. Chem. 2013, 67, 310-324;
Y. Kong, P. R. Boggu, G. M. Park, Y. S. Kim, S. H. An, I. S. Kim, Y. H. Jung, Molecules 2022, 27, 2603.
C.-M. Che, V. K.-Y. Lo, C.-Y. Zhou, J.-S. Huang, Chem. Soc. Rev. 2011, 40, 1950-1975;
S. Enthaler, A. Company, Chem. Soc. Rev. 2011, 40, 4912-4924;
D. T. Ziegler, G. C. Fu, J. Am. Chem. Soc. 2016, 138, 12069-12072;
J. J. Sangster, J. R. Marshall, N. J. Turner, J. Mangas-Sanchez, ChemBioChem 2022, 23, e202100464;
J.-B. Feng, X.-F. Wu, Appl. Organomet. Chem. 2015, 29, 63-86;
R. Zhang, C.-Y. Song, Z. Sui, Y. Yuan, Y.-C. Gu, C. Chen, Chem. Rec. 2023, 23, e202300020.
M. Wolter, G. Nordmann, G. E. Job, Org. Lett. 2002, 4, 973-976;
Q. Cai, D. Ma, Org. Lett. 2003, 5, 3799-3802;
Q. Cai, B. Zou, D. Ma, Angew. Chem. Int. Ed. 2006, 45, 1276-1279;
X. Lv, W. Bao, J. Org. Chem. 2007, 72, 3863-3867;
A. Shafir, P. A. Lichtor, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3490-3491.
Y. Peng, G. Song, Green Chem. 2002, 4, 349-351;
J. A. Aikins, M. Haurez, J. R. Rizzo, J.-P. V. Hoeck, W. Brione, J.-P. Kestemont, C. Stevens, X. Lemair, G. A. Stephenson, E. Marlot, M. Forst, I. N. Houpis, J. Org. Chem. 2005, 70, 4695-4705;
A. De, S. Santra, I. A. Khalymbadzha, G. V. Zyryanov, A. Majee, Org. Biomol. Chem. 2021, 19, 1278-1286;
Y. Gong, Z. Zhu, Q. Qian, W. Zong, H. Gong, Org. Lett. 2021, 23, 1005-1010.
S. A. Weissman, K. Rossen, P. J. Reider, Org. Lett. 2001, 3, 2513-2513;
S. D. Lepore, Y. He, J. Org. Chem. 2003, 68, 8261-8263;
O. Renaudet, J.-L. Reymond, Org. Lett. 2004, 6, 397-400;
V. Satcharoen, N. J. McLean, S. C. Kemp, N. P. Camp, R. C. D. Brown, Org. Lett. 2007, 9, 1867-1869;
Y. Jung, I. Kim, J. Org. Chem. 2015, 80, 2001-2005;
R. K. Orr, L.-C. Campeau, H. R. Chobanian, H. M. McCabe Dunn, B. Pio, C. W. Plummer, A. Nolting, R. T. Ruck, Synthesis 2017, 49, 657-666;
M. Kaiser, D. Schönbauer, K. Schragl, M. Weil, P. Gaertner, V. S. Enev, J. Org. Chem. 2022, 87, 15333-15349.
C. G. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966-6967;
Y. Miller, L. Miao, A. S. Hosseini, S. R. Chemler, J. Am. Chem. Soc. 2012, 134, 12149-12156;
C. S. Sevov, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 9303-9306;
H. Shigehisa, T. Aoki, S. Yamaguchi, N. Shimizu, K. Hiroya, J. Am. Chem. Soc. 2013, 135, 10306-10309;
M. Weiser, S. Hermann, A. Penner, H.-A. Wagenknecht, Beilstein J. Org. Chem. 2015, 11, 568-575;
M. J. Harper, E. J. Emmett, J. F. Bower, C. A. Russell, J. Am. Chem. Soc. 2017, 139, 12386-12389;
C. Luo, J. S. Bandar, J. Am. Chem. Soc. 2018, 140, 3547-3550.
T. Shintou, T. Mukaiyama, J. Am. Chem. Soc. 2004, 126, 7359-7367;
M. Murai, K. Origuchi, K. Takai, Org. Lett. 2014, 16, 3828-3831;
J. Kim, D.-H. Lee, N. Kalutharage, C. S. Yi, ACS Catal. 2014, 4, 3881-3885;
Y. Liu, X. Wang, Y. Wang, C. Du, H. Shi, S. Jin, C. Jiang, J. Xiao, M. Cheng, Adv. Synth. Catal. 2015, 357, 1029-103;
Q. Xu, H. Xie, P. Chen, L. Yu, J. Chen, X. Hu, Green Chem. 2015, 17, 2774-2779;
T. Kang, K. L. White, T. J. Mann, A. H. Hoveyda, M. Movassaghi, Angew. Chem. Int. Ed. 2017, 56, 13857-1386;
M. Miyauchi, T. Hiraoka, V. S. Raut, N. Asao, Chem. Commun. 2023, 59, 1221-1224.
H. Hu, S.-J. Chen, M. Mandal, S. M. Pratik, J. A. Buss, S. W. Krska, C. J. Cramer, S. S. Stahl, Nat. Catal. 2020, 3, 358-367.
B. J. Lee, K. S. DeGlopper, T. P. Yoon, Angew. Chem. Int. Ed. 2020, 59, 197-202;
M. Dong, Y. Jia, W. Zhou, J. Gao, X. Lv, F. Luo, Y. Zhang, S. Liu, Org. Chem. Front. 2021, 8, 6881-6887;
Y. Zhang, P. K. Sahoo, P. Ren, Y. Qin, R. Cauwenbergh, P. Nimmegeers, G. SivaRaman, S. Van Passel, A. Guidetti, S. Das, Chem. Commun. 2022, 58, 11454-11457;
C. Bo, F. Chen, Q. Bu, Z.-H. Du, M. Li, B. Dai, N. Liu, J. Org. Chem. 2023, 88, 3532-3538.
H. Wang, K. Liang, W. Xiong, S. Samanta, W. Li, A. Lei, Sci. Adv. 2020, 6, eaaz0590;
S. Chowdhury, S. Pandey, Asian J. Org. Chem. 2021, 10, 2902-2906;
N. Chen, H.-C. Xu, Chem. Rec. 2021, 21, 2306-2319.
N. R. Patel, R. A. Flowers, J. Am. Chem. Soc. 2013, 135, 4672-4675;
G. W. Wang, M. X. Cheng, R. S. Ma, S. D. Yang, Chem. Commun. 2015, 51, 6308-6311;
J. J. Ma, W. Yi, G. Lu, C. Cai, Org. Biomol. Chem. 2015, 13, 2890-2894;
J.-B. Feng, D. Wei, J.-L. Gong, X. Qi, X.-F. Wu, Tetrahedron Lett. 2014, 55, 5082-5084;
J.-X. Xu, C.-S. Kuai, X.-F. Wu, J. Org. Chem. 2022, 87, 6371-6377.