C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
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1 C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015
2 New strategies in organic synthesis nsf-cchf.com
3 What is C H Functionalization? D. Sames, et al. Science 2006, 312,
4 What is C H Functionalization? D. Sames, et al. Science 2006, 312,
5 What is not C H Functionalization? Friedel-Crafts acylation/alkylation Oxidative phenol-phenol coupling Allylic oxidation via SeO 2 or other stoichiometric transition metal Ortho- or remote-metalation via stoichiometric strong bases K. Itami, et al. Angew. Chem. Int. Ed. 2012, 51,
6 Content Examples in complex molecule synthesis C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Pd-cat. Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Oxidation C H Borylation C H Halogenation Two Total Syntheses Utilizing C H Functionalization
7 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation K. Fagnou, et al. J. Org. Chem. 2008, 73, 5022.
8 Aromatic C H Arylation D. Trauner, et al. Org. Lett. 2005, 7,
9 Aromatic C H Arylation D. Trauner, et al. Org. Lett. 2005, 7,
10 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation
11 C(sp 2 ) H Alkenylation and Alkylation R.G. Bergman, J.A. Ellman, et al. J. Am. Chem. Soc. 2005, 127,
12 C(sp 2 ) H Alkenylation and Alkylation R.G. Bergman, J.A. Ellman, et al. J. Am. Chem. Soc. 2005, 127,
13 C(sp 2 ) H Alkenylation and Alkylation R.G. Bergman, J.A. Ellman, et al. J. Am. Chem. Soc. 2005, 127,
14 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization
15 Directed C(sp 3 ) H Functionalization D. Sames, et al. J. Am. Chem. Soc. 2002, 124,
16 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion Metal Carbenoids
17 C H Insertion of Metal Carbenoids X. Lei, et al. J. Am. Chem. Soc. 2015, 137,
18 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes)
19 C H Amination (Nitrene Insertion) H. Tokuyama, et al. Angew. Chem. Int. Ed. 2010, 49,
20 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids)
21 C H Amination (C H Insertion of Metal Nitrenoids) J. Du Bois, et al. J. Am. Chem. Soc. 2003, 125,
22 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Oxidation (Pd-Catalyzed) M. White, et al. J. Am. Chem. Soc., 2005, 127, M. White, et al. Nature Chem. 2009, 125,
23 C H Allylic Oxidation (Pd-Catalyzed) M. White, et al. Nature Chem. 2009, 125,
24 C H Allylic Oxidation (Pd-Catalyzed) M. White, et al. Nature Chem. 2009, 125,
25 C H Allylic Oxidation (Pd-Catalyzed) M. White, et al. Nature Chem. 2009, 125,
26 C H Allylic Oxidation (Pd-Catalyzed) M. White, et al. Nature Chem. 2009, 125,
27 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Oxidation (Pd-Catalyzed) C H Borylation
28 C H Borylation J. F. Hartwig, et al. J. Am. Chem. Soc. 2011, 133,
29 Types of C H Functionalization C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Amination/Oxidation (Pd-Catalyzed) C H Borylation C H Halogenation (Metal-Catalyzed)
30 C H Halogenation K. Itami, et al. Angew. Chem. Int. Ed. 2012, 51,
31 Content Examples in complex molecule synthesis C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Pd-cat. Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Oxidation C H Borylation C H Halogenation Two Total Syntheses Utilizing C H Functionalization
32 (+)-Austamide Y. Kishi, et al. J. Am. Chem. Soc. 1979, 101, E. J. Corey, J. Am. Chem. Soc. 2002, 124,
33 (+)-Austamide E. J. Corey, J. Am. Chem. Soc. 2002, 124,
34 (+)-Austamide E. J. Corey, J. Am. Chem. Soc. 2002, 124,
35 E. J. Corey, J. Am. Chem. Soc. 2002, 124, (+)-Austamide
36 Dragmacidin D B. M. Stoltz, et al. J. Am. Chem. Soc. 2002, 124, K. Itami, et al. J. Am. Chem. Soc. 2011, 133,
37 Dragmacidin D K. Itami, et al. J. Am. Chem. Soc. 2011, 133,
38 Dragmacidin D K. Itami, et al. J. Am. Chem. Soc. 2011, 133,
39 Dragmacidin D K. Itami, et al. J. Am. Chem. Soc. 2011, 133,
40 Dragmacidin D K. Itami, et al. J. Am. Chem. Soc. 2011, 133,
41 K. Itami, et al. J. Am. Chem. Soc. 2011, 133, Dragmacidin D
42 Comparing total syntheses K. Itami, et al. Angew. Chem. Int. Ed. 2012, 51,
43 Summary Examples in complex molecule synthesis C-C Bond Formation Aromatic C H Arylation C(sp 2 ) H Alkenylation and Alkylation Pd-cat. Directed C(sp 3 ) H Functionalization C H Insertion of Metal Carbenoids C Heteroatom Bond Formation C H Amination (C H Insertion of Nitrenes) C H Amination (C H Insertion of Metal Nitrenoids) C H Allylic Oxidation C H Borylation C H Halogenation Two Total Syntheses Utilizing C H Functionalization
Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
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