doi: 10.1021/acs.orglett.0c01294.
Epub 2020 May 14.
Blue Light Promoted Difluoroalkylation of Aryl Ketones: Synthesis of Quaternary Alkyl Difluorides and Tetrasubstituted Monofluoroalkenes
Affiliations
- PMID: 32407104
- DOI: 10.1021/acs.orglett.0c01294
Item in Clipboard
Blue Light Promoted Difluoroalkylation of Aryl Ketones: Synthesis of Quaternary Alkyl Difluorides and Tetrasubstituted Monofluoroalkenes
Org Lett.
.
Abstract
A facile and cost-effective method for the preparation of fluoroalkylated compounds has been described by the direct photoexcitation of halofluoroalkanes with blue light absorptivity, enabling the difluoroalkylation of aryl ketones. The methodology has provided an efficient, mild, and catalyst-free synthetic method for quaternary difluoroalkylated arenes and tetrasubstituted monofluoroalkenes.
Similar articles
-
Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides.Chem Sci. 2019 Aug 20;10(40):9285-9291. doi: 10.1039/c9sc02806d. eCollection 2019 Oct 28. Chem Sci. 2019. PMID: 32055314 Free PMC article.
-
Cobalt-catalyzed difluoroalkylation of tertiary aryl ketones for facile synthesis of quaternary alkyl difluorides.Nat Commun. 2018 Nov 23;9(1):4951. doi: 10.1038/s41467-018-07525-y. Nat Commun. 2018. PMID: 30470757 Free PMC article.
-
Transition-Metal (Cu, Pd, Ni)-Catalyzed Difluoroalkylation via Cross-Coupling with Difluoroalkyl Halides.Acc Chem Res. 2018 Sep 18;51(9):2264-2278. doi: 10.1021/acs.accounts.8b00230. Epub 2018 Aug 22. Acc Chem Res. 2018. PMID: 30132322
-
Nickel-catalyzed cross-coupling of functionalized difluoromethyl bromides and chlorides with aryl boronic acids: a general method for difluoroalkylated arenes.Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9909-13. doi: 10.1002/anie.201405653. Epub 2014 Jul 17. Angew Chem Int Ed Engl. 2014. PMID: 25044391
-
Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol and Mannich-type reactions.Chem Rec. 2011 Sep;11(5):260-8. doi: 10.1002/tcr.201100020. Epub 2011 Sep 6. Chem Rec. 2011. PMID: 21898777 Review.
Cited by
-
Mechanochemical Synthesis of α-halo Alkylboronic Esters.Adv Sci (Weinh). 2024 Sep;11(33):e2404071. doi: 10.1002/advs.202404071. Epub 2024 Jul 3. Adv Sci (Weinh). 2024. PMID: 38958542 Free PMC article.
-
Cobalt-catalyzed decarboxylative difluoroalkylation of nitrophenylacetic acid salts.Chem Sci. 2023 Nov 16;14(47):13902-13907. doi: 10.1039/d3sc05583c. eCollection 2023 Dec 6. Chem Sci. 2023. PMID: 38075641 Free PMC article.
-
Silver-Promoted Radical Cascade Aryldifluoromethylation/Cyclization of 2-Allyloxybenzaldehydes for the Synthesis of 3-Aryldifluoromethyl-Containing Chroman-4-one Derivatives.Molecules. 2023 Apr 19;28(8):3578. doi: 10.3390/molecules28083578. Molecules. 2023. PMID: 37110812 Free PMC article.
-
Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers.Beilstein J Org Chem. 2024 Oct 24;20:2691-2703. doi: 10.3762/bjoc.20.226. eCollection 2024. Beilstein J Org Chem. 2024. PMID: 39469295 Free PMC article.
LinkOut - more resources
Full Text Sources
