Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent - PubMed
- ️Thu Jan 01 2015
. 2015 Jul 28;51(59):11848-51.
doi: 10.1039/c4cc09790d.
Affiliations
- PMID: 26108194
- DOI: 10.1039/c4cc09790d
Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent
Wei Su et al. Chem Commun (Camb). 2015.
Abstract
Rh(III)-catalyzed direct vinylic C-H cyanation reaction has been developed as a practical method for the synthesis of alkenyl nitriles. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation. Both acrylamides and ketoximes can be employed in the new C-H cyanation process.
Similar articles
-
Rhodium-catalyzed directed C-H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide.
Gong TJ, Xiao B, Cheng WM, Su W, Xu J, Liu ZJ, Liu L, Fu Y. Gong TJ, et al. J Am Chem Soc. 2013 Jul 24;135(29):10630-3. doi: 10.1021/ja405742y. Epub 2013 Jul 12. J Am Chem Soc. 2013. PMID: 23822812
-
Han J, Pan C, Jia X, Zhu C. Han J, et al. Org Biomol Chem. 2014 Nov 21;12(43):8603-6. doi: 10.1039/c4ob01736f. Org Biomol Chem. 2014. PMID: 25268970
-
Rhodium-Catalyzed Cyanation of C(sp(2))-H Bond of Alkenes.
Chaitanya M, Anbarasan P. Chaitanya M, et al. Org Lett. 2015 Aug 7;17(15):3766-9. doi: 10.1021/acs.orglett.5b01746. Epub 2015 Jul 21. Org Lett. 2015. PMID: 26196156
-
Cui J, Song J, Liu Q, Liu H, Dong Y. Cui J, et al. Chem Asian J. 2018 Mar 2;13(5):482-495. doi: 10.1002/asia.201701611. Epub 2018 Feb 15. Chem Asian J. 2018. PMID: 29446549 Review.
-
Synthesis of aromatic nitriles using nonmetallic cyano-group sources.
Kim J, Kim HJ, Chang S. Kim J, et al. Angew Chem Int Ed Engl. 2012 Nov 26;51(48):11948-59. doi: 10.1002/anie.201206168. Epub 2012 Nov 6. Angew Chem Int Ed Engl. 2012. PMID: 23132837 Review.
Cited by
-
Metal-Free Direct C-H Cyanation of Alkenes.
Wang X, Studer A. Wang X, et al. Angew Chem Int Ed Engl. 2018 Sep 3;57(36):11792-11796. doi: 10.1002/anie.201807303. Epub 2018 Aug 6. Angew Chem Int Ed Engl. 2018. PMID: 29995341 Free PMC article.
-
Recent Advances in Cyanamide Chemistry: Synthesis and Applications.
Prabhath MRR, Williams L, Bhat SV, Sharma P. Prabhath MRR, et al. Molecules. 2017 Apr 12;22(4):615. doi: 10.3390/molecules22040615. Molecules. 2017. PMID: 28417938 Free PMC article. Review.
-
Aldoxime dehydratases: production, immobilization, and use in multistep processes.
Martínková L, Kotik M, Kulik N, Křístková B, Šťastná K, Winkler M. Martínková L, et al. Appl Microbiol Biotechnol. 2024 Nov 15;108(1):518. doi: 10.1007/s00253-024-13272-6. Appl Microbiol Biotechnol. 2024. PMID: 39545989 Free PMC article. Review.
-
Dongbang S, Ellman JA. Dongbang S, et al. Angew Chem Int Ed Engl. 2021 Jan 25;60(4):2135-2139. doi: 10.1002/anie.202010735. Epub 2020 Nov 23. Angew Chem Int Ed Engl. 2021. PMID: 33017508 Free PMC article.
-
E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis.
Mu Y, Nguyen TT, Koh MJ, Schrock RR, Hoveyda AH. Mu Y, et al. Nat Chem. 2019 May;11(5):478-487. doi: 10.1038/s41557-019-0233-x. Epub 2019 Apr 1. Nat Chem. 2019. PMID: 30936524 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources