Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp(2) ) and C(sp) Centers
- PMID: 26178870
- DOI: 10.1002/chem.201501475
Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp(2) ) and C(sp) Centers
Abstract
Fluorine chemistry is a field undergoing tremendous expansion. Although much attention has been paid to the introduction of the fluorine atom and the CF3 group, less interest has been devoted to the introduction of functionalized fluorinated building blocks, in sharp contrast with the high versatility of the fluorinated products. In this Minireview, the most relevant methods for the introduction of difluoromethylated building blocks are summarized. Access to difluoromethylated arenes, alkenes, and alkynes is highlighted and special attention is paid to explanation of the reaction mechanism.
Keywords: alkenes; arenes; fluorine; reaction mechanisms; synthetic methods.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Recent progress in direct introduction of fluorinated groups on alkenes and alkynes by means of C-H bond functionalization.Chemistry. 2014 Dec 15;20(51):16830-45. doi: 10.1002/chem.201404537. Epub 2014 Oct 27. Chemistry. 2014. PMID: 25349030
-
Selective incorporation of difluoromethylene moieties into arenes assisted by transition metals.Chimia (Aarau). 2014;68(6):414-8. doi: 10.2533/chimia.2014.414. Chimia (Aarau). 2014. PMID: 25198751
-
Catalytic generation of α-CF3 enolate: direct catalytic asymmetric Mannich-type reaction of α-CF3 amide.J Am Chem Soc. 2014 Dec 31;136(52):17958-61. doi: 10.1021/ja511458k. Epub 2014 Dec 19. J Am Chem Soc. 2014. PMID: 25495289
-
Synthesis of fluorinated chiral amines using N-tert-butylsulfinyl imines.Future Med Chem. 2009 Aug;1(5):875-88. doi: 10.4155/fmc.09.62. Future Med Chem. 2009. PMID: 21426086 Review.
-
Synthetic approaches to monofluoroalkenes.Chem Soc Rev. 2011 May;40(5):2867-908. doi: 10.1039/c0cs00201a. Epub 2011 Mar 11. Chem Soc Rev. 2011. PMID: 21399789 Review.
Cited by
-
Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction.Org Lett. 2022 Mar 18;24(10):2002-2007. doi: 10.1021/acs.orglett.2c00438. Epub 2022 Mar 8. Org Lett. 2022. PMID: 35258311 Free PMC article.
-
The Fascinating Chemistry of α-Haloamides.ChemistryOpen. 2020 Jan 13;9(2):100-170. doi: 10.1002/open.201900220. eCollection 2020 Feb. ChemistryOpen. 2020. PMID: 32025460 Free PMC article. Review.
-
A Base-Promoted Reductive Coupling Platform for the Divergent Defluorofunctionalization of Trifluoromethylarenes.J Am Chem Soc. 2022 Jul 27;144(29):13032-13038. doi: 10.1021/jacs.2c05044. Epub 2022 Jul 14. J Am Chem Soc. 2022. PMID: 35833781 Free PMC article.
-
Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.Nat Commun. 2017 Nov 13;8(1):1460. doi: 10.1038/s41467-017-01540-1. Nat Commun. 2017. PMID: 29133781 Free PMC article.
-
(Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes.Chem Sci. 2022 Mar 2;13(12):3454-3460. doi: 10.1039/d1sc07061d. eCollection 2022 Mar 24. Chem Sci. 2022. PMID: 35432852 Free PMC article.
LinkOut - more resources
Full Text Sources