Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters
- PMID: 35509472
- PMCID: PMC9006967
- DOI: 10.1039/d2sc00968d
Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters
Abstract
Herein we describe the first construction of fluorinated tertiary stereocenters based on an alkene C(sp2)-C(sp2) bond cleavage. The new process, that takes advantage of a Rh-catalyzed carbyne transfer, relies on a branched-selective fluorination of tertiary allyl cations and is distinguished by a wide scope including natural products and drug molecule derivatives as well as adaptability to radiofluorination.
This journal is © The Royal Society of Chemistry.
Conflict of interest statement
There are no conflicts to declare.
References
-
- Pacheco M. C. Purser S. Gouverneur V. Chem. Rev. 2008;108:1943. doi: 10.1021/cr068410e. - DOI - PubMed
- O’hagan D. Chem. Soc. Rev. 2008;37:308. doi: 10.1039/B711844A. - DOI - PubMed
- Liang T. Neumann C. N. Ritter T. Angew. Chem., Int. Ed. 2013;52:8214. doi: 10.1002/anie.201206566. - DOI - PubMed
- Zhu Y. Han J. Wang J. Shibata N. Sodeoka M. Soloshonok V. A. Coelho J. A. S. Toste F. D. Chem. Rev. 2018;118:3887. doi: 10.1021/acs.chemrev.7b00778. - DOI - PMC - PubMed
- Szpera R. Moseley D. F. J. Smith L. B. Sterling A. J. Gouverneur V. Angew. Chem., Int. Ed. 2019;58:14824. doi: 10.1002/anie.201814457. - DOI - PubMed
- Sorlin A. M. Usman F. O. English C. K. Nguyen H. M. ACS Catal. 2020;10:11980. doi: 10.1021/acscatal.0c03493. - DOI
-
- Hagmann W. K. J. Med. Chem. 2008;51:4359. doi: 10.1021/jm800219f. - DOI - PubMed
- Purser S. Moore P. R. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008;37:320. doi: 10.1039/B610213C. - DOI - PubMed
- Gillis E. P. Eastman K. J. Hill M. D. Donnelly D. J. Meanwell N. A. J. Med. Chem. 2015;58:8315. doi: 10.1021/acs.jmedchem.5b00258. - DOI - PubMed
- Zhou Y. Wang J. Gu Z. Wang S. Zhu W. Aceña J. L. Soloshonok V. A. Izawa K. Liu H. Chem. Rev. 2016;116:422. doi: 10.1021/acs.chemrev.5b00392. - DOI - PubMed
- Inoue M. Sumii Y. Shibata N. ACS Omega. 2020;5:10633. doi: 10.1021/acsomega.0c00830. - DOI - PMC - PubMed
-
-
For recent selected examples:
- Greedy B. Paris J. M. Vidal T. Gouverneur V. Angew. Chem., Int. Ed. 2003;42:3291. doi: 10.1002/anie.200351405. - DOI - PubMed
- Phipps R. J. Hiramatsu K. Toste F. D. J. Am. Chem. Soc. 2012;134:8376. doi: 10.1021/ja303959p. - DOI - PubMed
- Wu J. Wang Y. M. Drljevic A. Rauniyar V. Phipps R. J. Dean Toste F. Proc. Natl. Acad. Sci. 2013;110:13729. doi: 10.1073/pnas.1304346110. - DOI - PMC - PubMed
- Yang X. Phipps R. J. Toste F. D. J. Am. Chem. Soc. 2014;136:5225. doi: 10.1021/ja500882x. - DOI - PMC - PubMed
- Yuan W. Szabõ K. J. Angew. Chem., Int. Ed. 2015;54:8533. doi: 10.1002/anie.201503373. - DOI - PMC - PubMed
- Guo R. Huang J. Zhao X. ACS Catal. 2018;8:926. doi: 10.1021/acscatal.7b03829. - DOI
- Wang Q. Lübcke M. Biosca M. Hedberg M. Eriksson L. Himo F. Szabó K. J. J. Am. Chem. Soc. 2020;142:20048. doi: 10.1021/jacs.0c09323. - DOI - PMC - PubMed
- Liu Z. Oxtoby L. J. Liu M. Li Z. Q. Tran V. T. Gao Y. Engle K. M. J. Am. Chem. Soc. 2021;143:8962. doi: 10.1021/jacs.1c03178. - DOI - PMC - PubMed
- Cao J. Wu H. Wang Q. Zhu J. Nat. Chem. 2021;13:671. doi: 10.1038/s41557-021-00698-y. - DOI - PMC - PubMed
-
-
-
For recent selected examples:
- Liang Y. Fu G. C. J. Am. Chem. Soc. 2014;136:5520. doi: 10.1021/ja501815p. - DOI - PMC - PubMed
- Jiao Z. Beiger J. J. Jin Y. Ge S. Zhou J. S. Hartwig J. F. J. Am. Chem. Soc. 2016;138:15980. doi: 10.1021/jacs.6b09580. - DOI - PubMed
- Balaraman K. Wolf C. Angew. Chem., Int. Ed. 2017;56:1390. doi: 10.1002/anie.201608752. - DOI - PMC - PubMed
- Butcher T. W. Hartwig J. F. Angew. Chem., Int. Ed. 2018;57:13125. doi: 10.1002/anie.201807474. - DOI - PubMed
- He Z. T. Jiang X. Hartwig J. F. J. Am. Chem. Soc. 2019;141:13066. doi: 10.1021/jacs.9b04440. - DOI - PubMed
- Liu J. Yuan Q. Toste F. D. Sigman M. S. Nat. Chem. 2019;11:710. doi: 10.1038/s41557-019-0289-7. - DOI - PMC - PubMed
- Butcher T. W. Yang J. L. Amberg W. M. Watkins N. B. Wilkinson N. D. Hartwig J. F. Nature. 2020;583:548. doi: 10.1038/s41586-020-2399-1. - DOI - PMC - PubMed
- Kalkman E. D. Hartwig J. F. J. Am. Chem. Soc. 2021;143:11741. doi: 10.1021/jacs.1c05346. - DOI - PMC - PubMed
-
For a review:
- Butcher T. W. Amberg W. M. Hartwig J. F. Angew. Chem., Int. Ed. 2022;61:1. doi: 10.1002/anie.202112251. - DOI - PubMed
-
-
-
For recent selected examples:
- Katcher M. H. Sha A. Doyle A. G. J. Am. Chem. Soc. 2011;133:15902. doi: 10.1021/ja206960k. - DOI - PubMed
- Topczewski J. J. Tewson T. J. Nguyen H. M. J. Am. Chem. Soc. 2011;133:19318. doi: 10.1021/ja2087213. - DOI - PubMed
- Liu W. Huang X. Cheng M. Nielsen R. J. Iii W. a G. Groves J. T. Science. 2012;337:1322. doi: 10.1126/science.1222327. - DOI - PubMed
- Braun M. Doyle A. G. J. Am. Chem. Soc. 2013;4:1.
- Lu Z. Zeng X. Hammond G. B. Xu B. J. Am. Chem. Soc. 2017;139:18202. doi: 10.1021/jacs.7b12704. - DOI - PMC - PubMed
- Bertrand X. Paquin J. F. Org. Lett. 2019;21:9759. doi: 10.1021/acs.orglett.9b03950. - DOI - PubMed
- Bafaluy D. Georgieva Z. Muñiz K. Angew. Chem., Int. Ed. 2020;59:14241. doi: 10.1002/anie.202004902. - DOI - PubMed
- Sharma H. A. Mennie K. M. Kwan E. E. Jacobsen E. N. J. Am. Chem. Soc. 2020;142:16090. doi: 10.1021/jacs.0c08150. - DOI - PMC - PubMed
- Tang H. J. Zhang X. Zhang Y. F. Feng C. Angew. Chem., Int. Ed. 2020;59:5242. doi: 10.1002/anie.201916471. - DOI - PubMed
- Tang H. J. Zhang B. Xue F. Feng C. Org. Lett. 2021;23:4040. doi: 10.1021/acs.orglett.1c01249. - DOI - PubMed
- Qian H. Chen J. Zhang B. Cheng Y. Xiao W.-J. Chen J.-R. Org. Lett. 2021;23:6987. doi: 10.1021/acs.orglett.1c02686. - DOI - PubMed
- Leibler I. N.-M. Tekle-Smith M. A. Doyle A. G. Nat. Commun. 2021;12:6950. doi: 10.1038/s41467-021-27165-z. - DOI - PMC - PubMed
- Zhang Y. Fitzpatrick A. N. Das M. Bedre I. P. Yayla H. G. Lall M. S. Musacchio P. Z. Chem. Catal. 2022;2:1. doi: 10.1016/j.checat.2021.12.020. - DOI
-
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