Selective Terminal Functionalization of Linear Alkanes.
Alkanes
Biocatalysis
C−H Activation
Metal-Walk
Synthetic Methods
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:
24 Jul 2023
24 Jul 2023
Historique:
received:
09
05
2023
medline:
27
5
2023
pubmed:
27
5
2023
entrez:
27
5
2023
Statut:
ppublish
Résumé
A two-step sequential strategy involving a biocatalytic dehydrogenation/remote hydrofunctionalization, as a unified and versatile approach to selectively convert linear alkanes into a large array of valuable functionalized aliphatic derivatives is reported. The dehydrogenation is carried out by a mutant strain of a bacteria Rhodococcus and the produced alkenes are subsequently engaged in a remote functionalization through a metal-catalyzed hydrometalation/migration sequence that subsequently react with a large variety of electrophiles. The judicious implementation of this combined biocatalytic and organometallic approach enabled us to develop a high-yielding protocol to site-selectively functionalize unreactive primary C-H bonds.
Identifiants
pubmed: 37243485
doi: 10.1002/anie.202306343
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202306343Subventions
Organisme : HORIZON EUROPE European Research Council
ID : 786976
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
J. F. Hartwig, M. A. Larsen, ACS Cent. Sci. 2016, 2, 281-292.
J. F. Hartwig, J. Am. Chem. Soc. 2016, 138, 2-24.
T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2012, 45, 826-839.
D. Sames, K. Godula, Science 2006, 312, 67-72.
J. F. Hartwig, Acc. Chem. Res. 2017, 50, 549-555.
K. I. Goldberg, A. S. Goldman, Acc. Chem. Res. 2017, 50, 620-626.
P. J. Pérez, Alkane C-H activation by single-site metal catalysis, Springer, Heidelberg, 2012.
H. Chen, S. Sclecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995-1997.
R. Oeschger, B. Su, I. Yu, C. Ehinger, E. Romero, S. He, J. F. Hartwig, Science 2020, 368, 736-741.
Y. K. Liao, Y.-F. Yang, Y. Li, J. N. Sanders, K. N. Houk, D. C. Musaev, H. M. L. Davies, Nat. Chem. 2018, 10, 1048-1055.
S. Popov, B. Shao, A. L. Bagdasarian, T. R. Benton, L. Zou, Z. Yang, K. N. Houk, H. M. Nelson, Science 2018, 361, 381-387.
B. Shao, A. L. Bagdasarian, S. Popov, H. M. Nelson, Science 2017, 355, 1403-1407.
C. Shu, A. Noble, V. K. Aggarwal, Nature 2020, 586, 714-720.
F. Juliá-Hernández, T. Moragas, J. Cornella, R. Martin, Nature 2017, 545, 84-88.
S. Dupuy, K. F. Zhang, A.-S. Goutierre, O. Baudoin, Angew. Chem. Int. Ed. 2016, 55, 14793-14797.
X. Jia, Z. Huang, Nat. Chem. 2016, 8, 157-161.
A. Vasseur, J. Bruffaerts, I. Marek, Nat. Chem. 2016, 8, 209-219.
H. Sommer, F. Julia-Hernandez, R. Martin, I. Marek, ACS Cent. Sci. 2018, 4, 153-165.
For a review, see: A. Kumar, T. M. Bhatti, A. S. Goldman, Chem. Rev. 2017, 117, 12357-12384.
A. F. Prusinowski, R. K. Twumasi, E. A. Wappes, D. A. Nagib, J. Am. Chem. Soc. 2020, 142, 5429-5438.
J. K. Kochi, J. Am. Chem. Soc. 1963, 85, 1958-1968.
B. Acott, A. L. J. Beckwith, Aust. J. Chem. 1964, 17, 1342-1353.
Z. Cekovic, M. M. Green, J. Am. Chem. Soc. 1974, 96, 3000-3002.
R. Breslow, S. Baldwin, T. Flechtner, P. Kalicky, S. Liu, W. Washburn, J. Am. Chem. Soc. 1973, 95, 3251-3262.
A. F. Voica, A. Mendoza, W. R. Gutekunst, J. O. Fraga, P. S. Baran, Nat. Chem. 2012, 4, 629-635.
M. Parasram, P. Chuentragool, Y. Wang, Y. Shi, V. Gevorgyan, J. Am. Chem. Soc. 2017, 139, 14857-14860.
P. Chuentragool, M. Parasram, Y. Shi, V. Gevorgyan, J. Am. Chem. Soc. 2018, 140, 2465-2468.
W. Jin, S. Yu, Org. Lett. 2021, 23, 6931-6935.
C. B. Bheeter, R. Jin, J. K. Bera, P. H. Dixneuf, H. Doucet, Adv. Synth. Catal. 2014, 356, 119-124.
L. M. Stateman, R. M. Dare, A. N. Paneque, D. A. Nagib, Chem 2022, 8, 210-224.
K. P. S. Cheung, S. Sarkar, V. Gevorgyan, Chem. Rev. 2022, 122, 1543-1625.
C. Wang, G. Dong, ACS Catal. 2020, 10, 6058-6070.
For a review, see: J. G. West, E. J. Sorensen, Isr. J. Chem. 2017, 57, 259-269.
M. Hönig, P. Sondermann, N. J. Turner, E. M. Carreira, Angew. Chem. Int. Ed. 2017, 56, 8942-8973.
J. C. Lewis, P. S. Coelho, F.-H. Arnold, Chem. Soc. Rev. 2011, 40, 2003-2021.
G. Qu, A. Li, C. G. Acevedo-Rocha, Z. Sun, M. T. Reetz, Angew. Chem. Int. Ed. 2020, 59, 13204-13231.
M. Ayala, E. Torres, Appl. Catal. A 2004, 272, 1-13, 10.1016/j.apcata.2004.05.046.
M. A. Bigi, M. A. Reed, M. C. White, Nat. Chem. 2011, 3, 216-222.
D. Kumar, S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2004, 126, 5072-5073.
S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, W. Thiel, Chem. Rev. 2010, 110, 949-1017.
K. Koike, K. Ara, S. Adachi, H. Takigawa, H. Mori, S. Inoue, Y. Kimura, S. Ito, Appl. Environ. Microbiol. 1999, 65, 5636-5638.
S. Singh, J. Bruffaerts, A. Vasseur, I. Marek, Nat. Commun. 2017, 8, 14200.
J. Bruffaerts, D. Pierrot, I. Marek, Nat. Chem. 2018, 10, 1164-1170.
J. V. Obligacion, P. J. Chirik, J. Am. Chem. Soc. 2013, 135, 19107-19110.
J. C. Saam, J. L. Speier, J. Am. Chem. Soc. 1958, 80, 4104-4106.
A. Masarwa, D. Didier, T. Zabrodski, M. Schinkel, L. Ackermann, I. Marek, Nature 2014, 505, 199-203.
T. Gibson, L. Tulich, J. Org. Chem. 1981, 46, 1821-1823.
A. E. Strom, J. F. Hartwig, J. Org. Chem. 2013, 78, 8909-8914.
F. Zhou, J. Zhu, Y. Zhang, S. Zhu, Angew. Chem. Int. Ed. 2018, 57, 4058-4062.
H. Klein, R. Jackstell, M. Beller, Chem. Commun. 2005, 2283-2285.
G.-H. Ho, L. Judkele, J. Bruffaerts, I. Marek, Angew. Chem. Int. Ed. 2018, 57, 8012-8016.
C. Romano, C. Mazet, J. Am. Chem. Soc. 2018, 140, 4743-4750.
G.-H. Ho, L. Segura, I. Marek, Chem. Sci. 2020, 11, 5944-5949.