C H Activated Trifluoromethylation
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1 Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013
2 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation of sp 2 -Hybridized C-H Bonds Trifluoromethylation of sp 3 -Hybridized C-H Bonds Summary & Acknowledgement 2
3 Background: Commercially Available Pharmaceuticals S. Roy Tetrahedron 2011, 27,
4 Background: Trifluoromethyl Sources 4
5 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation of sp 2 -Hybridized C-H Bonds Trifluoromethylation of sp 3 -Hybridized C-H Bonds Summary & Acknowledgement 5
6 Sp C-H : Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes F.-L. Qing J. Am. Chem. Soc. 2010, 132, F.-L. Qing Org. Lett., 2012, 14, F.-L. Qing J. Org. Chem. 2012, 77,
7 Sp C-H : Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes F.-L. Qing J. Org. Chem. 2012, 77, F.-L. Qing Eur. J. Org. Chem. 2012,
8 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation of sp 2 -Hybridized C-H Bonds Trifluoromethylation of sp 3 -Hybridized C-H Bonds Summary & Acknowledgement 8
9 Sp 2 C-H Trifluoromethylation 9
10 Sp 2 C-H (I): Copper-Catalyzed Trifluoromethylation of Terminal Alkenes Electrophilic Trifluoromethylating S. L. Buchwald Angew. Chem. Int. Ed. 2011, 50, J.-B. Wang J. Am. Chem. Soc. 2011, 133, L. Liu J. Am. Chem. Soc. 2011, 133,
11 Sp 2 C-H (I): Copper-Catalyzed Trifluoromethylation of Terminal Alkenes Mechanistic Rationale of Wang s J.-B. Wang J. Am. Chem. Soc. 2011, 133,
12 Sp 2 C-H (I): Copper-Catalyzed Trifluoromethylation of Terminal Alkenes Proposed mechanism and corresponding theoretical calculations of Liu s Heck-like four-membered-ring TS L. Liu J. Am. Chem. Soc. 2011, 133,
13 Sp 2 C-H (I): Copper-Catalyzed Trifluoromethylation of Terminal Alkenes Nucleophilic Trifluoromethylating F.-L. Qing Org. Lett., 2012, 14,
14 Sp 2 C-H (I): Palladium-Catalyzed Oxidative Trifluoromethylation of Activated Alkenes G.-S. Liu J. Am. Chem. Soc. 2012, 134,
15 Sp 2 C-H (I): Rhodium-Catalyzed Trifluoromethylation of α, β -Unsaturated Ketones I. Kumadaki Org. Lett. 2004, 6,
16 Sp 2 C-H Trifluoromethylation (II) 16
17 Sp 2 C-H (II): Silver-Mediated Trifluoromethylation of Arenes TMSCF 3 as a precursor to radical arene trifluoromethylation excess of required aromatic compound a low regioselectivity M. S. Sanford Org. Lett. 2011, 13,
18 Sp 2 C-H (II): Silver-Mediated Ortho-Trifluoromethylation of Functionalized Aromatic Triazenes P. S. Bräse Angew. Chem. Int. Ed. 2012, 51,
19 Sp 2 C-H Trifluoromethylation (II) 19
20 Sp 2 C-H (II): Rhenium-Catalyzed Trifluoromethylation of Arenes and Heteroarenes using MTO as catalyst A. Togni ACS Catal. 2012, 2,
21 Sp 2 C-H Trifluoromethylation (II) 21
22 Sp 2 C-H (II): Palladium-Catalyzed ortho-trifluoromethylation of Arenes J.-Q. Yu J. Am. Chem. Soc. 2010, 132, J.-Q. Yu J. Am. Chem. Soc. 2012, 134,
23 Sp 2 C-H (II): Palladium-Catalyzed ortho-trifluoromethylation of Arenes Z.-J. Shi Org. Lett. 2013, 15,
24 Sp 2 C-H (II): Trifluoromethylation with CF3+ reagents via a Monomeric Palladium(IV) Complex. M. S. Sanford J. Am. Chem. Soc. 2010, 132,
25 Sp 2 C-H (II): Iridium-Catalyzed Selective Trifluoromethylation of 1,3-Disubstituted Arenes iridium-catalyzed borylation and copper-catalyzed trifluoromethylation of arenes a variety of functional groups could be tolerated, which might lead to a number of biologically active molecules J. F. Hartwig Angew. Chem. Int. Ed. 2012, 51, Q. Shen Angew. Chem. Int. Ed. 2012, 51,
26 Sp 2 C-H Trifluoromethylation (III) 26
27 Sp 2 C-H (III): Innate C-H Trifluoromethylation of Heterocycles P. S. Bräse, PNAS, 2011, 108,
28 Sp 2 C-H (III): Innate C-H Trifluoromethylation of Heterocycles P. S. Bräse, PNAS, 2011, 108,
29 Sp 2 C-H (III): Iron(II)-catalyzed trifluoromethylation of aromatic and heteroaromatic compounds The regioselectivity is oriented by the general trend of electrophilic substitution of aromatic compounds with some exceptions. T. Yamakawa J. Fluorine Chem. 2010, 131,
30 Sp 2 C-H (III): Trifluoromethylation of Arenes and Heteroarenes by Photoredox Catalysis D. W. C. MacMillan, Nature, 2011, 480,
31 Sp 2 C-H (III): Trifluoromethylation of Arenes and Heteroarenes by Photoredox Catalysis wide substrate scope D. W. C. MacMillan, Nature, 2011, 480,
32 Sp 2 C-H (III): Trifluoromethylation of Arenes and Heteroarenes by Photoredox Catalysis Application in the synthesis of Lipitor D. W. C. MacMillan, Nature, 2011, 480,
33 Sp 2 C-H (III): Copper-Catalyzed Direct C H Oxidative Trifluoromethylation of Heteroarenes F.-L. Qing J. Am. Chem. Soc. 2012, 134,
34 Sp 2 C-H (III): Copper-Catalyzed Direct C H Oxidative Trifluoromethylation of Heteroarenes F.-L. Qing J. Am. Chem. Soc. 2012, 134,
35 Sp 2 C-H Trifluoromethylation: Visible light-induced trifluoromethylation E. J. Cho Tetrahedron Lett. 2012, 53,
36 Sp 2 C-H (III): Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles G. Liu Chem. Eur. J. 2011, 17, M. Sodeoka, Tetrahedron Lett. 2010, 51,
37 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation of sp 2 -Hybridized C-H Bonds Trifluoromethylation of sp 3 -Hybridized C-H Bonds Summary & Acknowledgement 37
38 Sp 3 C-H : Photoredox Organocatalyzed Enantioselective α-trifluoromethylation of Aldehydes D. W. C. MacMillan J. Am. Chem. Soc. 2009, 131,
39 Sp 3 C-H : Photoredox Organocatalyzed Enantioselective α-trifluoromethylation of Aldehydes D. W. C. MacMillan J. Am. Chem. Soc. 2009, 131,
40 Sp 3 C-H : Trifluoromethylation of Tetrahydroisoquinoline and amines F.-L. Qing Chem. Commun. 2010, 46, C.-J. Li Tetrahedron Lett. 2011, 52,
41 Sp 3 C-H : Oxidative C-H Functionalisation of Tertiary Amines C-H. Tan Green Chem. 2011, 13,
42 Sp 3 C-H : Ru-Catalyzed Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones A. Zakarian J. Am. Chem. Soc. 2012, 134,
43 Sp 3 C-H : Ru-Catalyzed Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones A. Zakarian J. Am. Chem. Soc. 2012, 134,
44 Sp 3 C-H : Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-ketoesters L. H. Gade J. Am. Chem. Soc. 2012, 134,
45 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation of sp 2 -Hybridized C-H Bonds Trifluoromethylation of sp 3 -Hybridized C-H Bonds Summary & Acknowledgement 45
46 Summary: New Catalyst Regioselectivity.. Enantioselectivity WHAT CAN WE DO NEXT? 46
47 Acknowledgement: Prof. Yong Huang All members of E201 All of you Here Thank you for your attention! 47
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