Effect of the Ligand Backbone on the Reactivity and Mechanistic Paradigm of Non-Heme Iron(IV)-Oxo during Olefin Epoxidation.
biomimetic synthesis
epoxidation
ligand effects
non-heme iron-oxo
oxygen atom transfer
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:
14 06 2021
14 06 2021
Historique:
received:
18
02
2021
pubmed:
10
4
2021
medline:
10
4
2021
entrez:
9
4
2021
Statut:
ppublish
Résumé
The oxygen atom transfer (OAT) reactivity of the non-heme [Fe
Identifiants
pubmed: 33836110
doi: 10.1002/anie.202102484
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
14030-14039Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
J. Jasniewski, L. Que, Chem. Rev. 2018, 118, 2554-2592.
S. Sahu, D. P. Goldberg, J. Am. Chem. Soc. 2016, 138, 11410-11428.
M. Guo, T. Corona, K. Ray, W. Nam, ACS Cent. Sci. 2019, 5, 13-28.
M. Sankaralingam, Y.-M. Lee, W. Nam, S. Fukuzumi, Coord. Chem. Rev. 2018, 365, 41-59.
X. Huang, J. T. Groves, J. Biol. Inorg. Chem. 2017, 22, 185-207.
J. P. Biswas, S. Guin, D. Maiti, Coord. Chem. Rev. 2020, 408, 213174.
S. Rana, J. P. Biswas, S. Paul, A. Paik, D. Maiti, Chem. Soc. Rev. 2021, 50, 243.
R. P. Hausinger, Crit. Rev. Biochem. Mol. Biol. 2004, 39, 21-68.
E. G. Kovaleva, J. D. Lipscomb, Nat. Chem. Biol. 2008, 4, 186-193.
M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2888.
J. Rittle, M. T. Green, Science 2010, 330, 933-937.
S. Shaik, H. Hirao, D. Kumar, Nat. Prod. Rep. 2007, 24, 533-552.
T. G. Traylor, F. Xu, J. Am. Chem. Soc. 1988, 110, 1953-1958.
M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. Lopez de Laorden, R. Mas-Ballesté, M. Merz, L. Que, Jr., Angew. Chem. Int. Ed. 2006, 45, 3446-3449;
Angew. Chem. 2006, 118, 3524-3528.
P. Barman, A. K. Vardhaman, B. Martin, S. J. Wörner, C. V. Sastri, P. Comba, Angew. Chem. Int. Ed. 2015, 54, 2095-2099;
Angew. Chem. 2015, 127, 2123-2127.
O. Cussó, X. Ribas, J. Lloret-Fillol, M. Costas, Angew. Chem. Int. Ed. 2015, 54, 2729;
Angew. Chem. 2015, 127, 2767.
H. Park, H. M. Ahn, H. Y. Jeong, C. Kim, D. Lee, Chem. Eur. J. 2018, 24, 8632.
R. V. Ottenbacher, D. G. Samsonenko, E. P. Talsi, K. P. Bryliakov, ACS Catal. 2014, 4, 1599.
D. Sheet, T. K. Paine, Chem. Sci. 2016, 7, 5322.
O. Cussó, X. Ribas, M. Costas, Chem. Commun. 2015, 51, 14285.
G. Olivo, O. Cussó, M. Costas, Chem. Asian J. 2016, 11, 3148.
W. Wang, Q. Sun, D. Xu, C. Xia, W. Sun, ChemCatChem 2017, 9, 420.
M. Wu, C.-X. Miao, S. Wang, X. Hu, C. Xia, F. E. Kühn, W. Sun, Adv. Synth. Catal. 2011, 353, 3014.
O. Cussó, I. Garcia-Bosch, X. Ribas, J. Lloret-Fillol, M. Costas, J. Am. Chem. Soc. 2013, 135, 14871.
A. Bassan, M. R. A. Blomberg, P. E. M. Siegbahn, L. Que, Jr., Angew. Chem. Int. Ed. 2005, 44, 2939-2941;
Angew. Chem. 2005, 117, 2999-3001.
K. Chen, J. Q. Lawrence, Angew. Chem. Int. Ed. 1999, 38, 2227-2229;
Angew. Chem. 1999, 111, 2365-2368.
M. Costas, A. K. Tipton, K. Chen, D.-H. Jo, L. Que, J. Am. Chem. Soc. 2001, 123, 6722-6723.
R. Mas-Ballesté, M. Costas, T. van den Berg, L. Que, Jr., Chem. Eur. J. 2006, 12, 7489-7500.
R. Mas-Ballesté, L. Que, J. Am. Chem. Soc. 2007, 129, 15964-15972.
P. D. Oldenburg, Y. Feng, I. Pryjomska-Ray, D. Ness, L. Que, J. Am. Chem. Soc. 2010, 132, 17713-17723.
K. Suzuki, P. D. Oldenburg, L. Que, Jr., Angew. Chem. Int. Ed. 2008, 47, 1887-1889;
Angew. Chem. 2008, 120, 1913-1915.
A. M. Zima, O. Y. Lyakin, R. V. Ottenbacher, K. P. Bryliakov, E. P. Talsi, ACS Catal. 2017, 7, 60-69.
W. Nam, R. Ho, J. S. Valentine, J. Am. Chem. Soc. 1991, 113, 7052-7054.
X. Engelmann, D. D. Malik, T. Corona, K. Warm, E. R. Farquhar, M. Swart, W. Nam, K. Ray, Angew. Chem. Int. Ed. 2019, 58, 4012-4016;
Angew. Chem. 2019, 131, 4052-4056.
O. Y. Lyakin, R. V. Ottenbacher, K. P. Bryliakov, E. P. Talsi, ACS Catal. 2012, 2, 1196-1202.
R. V. Ottenbacher, D. G. Samsonenko, E. P. Talsi, K. P. Bryliakov, ACS Catal. 2016, 6, 979-988.
O. Cussó, I. Garcia-Bosch, D. Font, X. Ribas, J. Lloret-Fillol, M. Costas, Org. Lett. 2013, 15, 6158-6161.
R. A. Baglia, C. M. Krest, T. Yang, P. Leeladee, D. P. Goldberg, Inorg. Chem. 2016, 55, 10800-10809.
J. Du, C. Miao, C. Xia, Y.-M. Lee, W. Nam, W. Sun, ACS Catal. 2018, 8, 4528-4538.
K. P. Bryliakov, Chem. Rev. 2017, 117, 11406-11459.
E. P. Talsi, K. P. Bryliakov, Coord. Chem. Rev. 2012, 256, 1418-1434.
K. P. Bryliakov, E. P. Talsi, Coord. Chem. Rev. 2014, 276, 73-96.
B. Qiu, D. Xu, Q. Sun, C. Miao, Y.-M. Lee, X.-X. Li, W. Nam, W. Sun, ACS Catal. 2018, 8, 2479-2487.
D. Shen, B. Qiu, D. Xu, C. Miao, C. Xia, W. Sun, Org. Lett. 2016, 18, 372-375.
M. Wu, B. Wang, S. Wang, C. Xia, W. Sun, Org. Lett. 2009, 11, 3622-3625.
J. Park, Y.-M. Lee, K. Ohkubo, W. Nam, S. Fukuzumi, Inorg. Chem. 2015, 54, 5806-5812.
S. Rana, J. P. Biswas, A. Sen, M. Clémancey, G. Blondin, J.-M. Latour, G. Rajaraman, D. Maiti, Chem. Sci. 2018, 9, 7843-7858.
W. Rasheed, A. Draksharapu, S. Banerjee, V. G. Young, Jr., R. Fan, Y. Guo, M. Ozerov, J. Nehrkorn, J. Krzystek, J. Telser, et al., Angew. Chem. Int. Ed. 2018, 57, 9387-9391;
Angew. Chem. 2018, 130, 9531-9535.
D. Macikenas, E. Skrzypczak-Jankun, J. D. Protasiewicz, J. Am. Chem. Soc. 1999, 121, 7164-7165;
Also the minimal acid impuritiy present in idomesitylene diacetate might have role in enhancing the epoxidation product formation.
S. Rana, A. Dey, D. Maiti, Chem. Commun. 2015, 51, 14469-14472.
M. Ghosh, K. K. Singh, C. Panda, A. Weitz, M. P. Hendrich, T. J. Collins, B. B. Dhar, S. Sen Gupta, J. Am. Chem. Soc. 2014, 136, 9524-9527.
K. K. Singh, M. K. Tiwari, B. B. Dhar, K. Vanka, S. Sen Gupta, Inorg. Chem. 2015, 54, 6112-6121.
S. Jana, M. Ghosh, M. Ambule, S. Sen Gupta, Org. Lett. 2017, 19, 746-749.
G. Olivo, O. Lanzalunga, S. Di Stefano, Adv. Synth. Catal. 2016, 358, 843-863.
R. D. Arasasingham, G. X. He, T. C. Bruice, J. Am. Chem. Soc. 1993, 115, 7985-7991.
J. M. Garrison, D. Ostovic, T. C. Bruice, J. Am. Chem. Soc. 1989, 111, 4960-4966.
G. Coin, R. Patra, S. Rana, J. P. Biswas, P. Dubourdeaux, M. Clémancey, S. P. de Visser, D. Maiti, P. Maldivi, J.-M. Latour, ACS Catal. 2020, 10, 10010-10020.
T. G. Traylor, A. R. Miksztal, J. Am. Chem. Soc. 1989, 111, 7443-7448.
E. G. Samsel, K. Srinivasan, J. K. Kochi, J. Am. Chem. Soc. 1985, 107, 7606-7617.
Y. Naruta, F. Tani, N. Ishihara, K. Maruyama, J. Am. Chem. Soc. 1991, 113, 6865-6872.
D. Ostovic, T. C. Bruice, Acc. Chem. Res. 1992, 25, 314-320.
C.-M. Che, C.-K. Li, W.-T. Tang, W.-Y. Yu, J. Chem. Soc. Dalton Trans. 1992, 3153-3158.
S. N. Dhuri, K.-B. Cho, Y.-M. Lee, S. Y. Shin, J. H. Kim, D. Mandal, S. Shaik, W. Nam, J. Am. Chem. Soc. 2015, 137, 8623-8632.
J. T. Groves, Y. Watanabe, J. Am. Chem. Soc. 1986, 108, 507-508.
B. Wang, Y.-M. Lee, M. Clémancey, M. S. Seo, R. Sarangi, J.-M. Latour, W. Nam, J. Am. Chem. Soc. 2016, 138, 2426-2436.
A. D. N. Vaz, D. F. McGinnity, M. J. Coon, Proc. Natl. Acad. Sci. USA 1998, 95, 3555-3560.
M. Yonemitsu, Y. Tanaka, M. Iwamoto, J. Catal. 1998, 178, 207-213.
M. Ansari, N. Vyas, A. Ansari, G. Rajaraman, Dalton Trans. 2015, 44, 15232-15243.
A. Ansari, A. Kaushik, G. Rajaraman, J. Am. Chem. Soc. 2013, 135, 4235-4249.
A. Ansari, M. Ansari, A. Singha, G. Rajaraman, Chem. Eur. J. 2017, 23, 10110-10125.
S. Shaik, H. Hirao, D. Kumar, Acc. Chem. Res. 2007, 40, 532-542.
T. A. Jackson, J.-U. Rohde, M. S. Seo, C. V. Sastri, R. DeHont, A. Stubna, T. Ohta, T. Kitagawa, E. Münck, W. Nam, et al., J. Am. Chem. Soc. 2008, 130, 12394-12407.
J.-U. Rohde, S. Torelli, X. Shan, M. H. Lim, E. J. Klinker, J. Kaizer, K. Chen, W. Nam, L. Que, J. Am. Chem. Soc. 2004, 126, 16750-16761.
G. Mukherjee, A. Alili, P. Barman, D. Kumar, C. V. Sastri, S. P. de Visser, Chem. Eur. J. 2019, 25, 5086-5098.
M. Ansari, D. Senthilnathan, G. Rajaraman, Chem. Sci. 2020, 11, 10669-10687.
R. Kumar, B. Pandey, A. Sen, M. Ansari, S. Sharma, G. Rajaraman, Coord. Chem. Rev. 2020, 419, 213397.
M. Puri, L. Que, Acc. Chem. Res. 2015, 48, 2443-2452.
D. Schröder, S. Shaik, H. Schwarz, Acc. Chem. Res. 2000, 33, 139-145.
F. Wang, W. Sun, C. Xia, Y. Wang, J. Biol. Inorg. Chem. 2017, 22, 987-998.
S. Shaik, D. Danovich, A. Fiedler, D. Schröder, H. Schwarz, Helv. Chim. Acta 1995, 78, 1393-1407.
F. P. Guengerich, T. L. Macdonald, Acc. Chem. Res. 1984, 17, 9-16.
J. Bautz, P. Comba, C. Lopez de Laorden, M. Menzel, G. Rajaraman, Angew. Chem. Int. Ed. 2007, 46, 8067-8070;
Angew. Chem. 2007, 119, 8213-8216.
J. N. Harvey, M. Aschi, Faraday Discuss. 2003, 124, 129-143.
D. Danovich, S. Shaik, J. Am. Chem. Soc. 1997, 119, 1773-1786.
P. Comba, G. Rajaraman, Inorg. Chem. 2008, 47, 78-93.
M. A. Sainna, S. Kumar, D. Kumar, S. Fornarini, M. E. Crestoni, S. P. de Visser, Chem. Sci. 2015, 6, 1516-1529.
D. Kumar, R. Latifi, S. Kumar, E. V. Rybak-Akimova, M. A. Sainna, S. P. de Visser, Inorg. Chem. 2013, 52, 7968-7979.
S. Shaik, H. Chen, D. Janardanan, Nat. Chem. 2011, 3, 19-27.
D. Lakk-Bogáth, G. Speier, J. Kaizer, Inorg. Chem. Commun. 2019, 107, 107446.
D. Kumar, H. Hirao, Q. Lawrence, S. Shaik, J. Am. Chem. Soc. 2005, 127, 8026-8027.
L. Bernasconi, E. J. Baerends, J. Am. Chem. Soc. 2013, 135, 8857.