Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed C-H Activation Using Dioxygen as the Oxidant
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1 Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed C- Activation Using Dioxygen as the xidant Zhuangzhi Shi, Chun Zhang, Si Li, Delin Pan, Shengtao Ding, Yuxin Cui, and ing Jiao Angew. Chem. Int. Ed. 2009, ASAP DI: /anie Marie-Céline Frantz Wipf Group, Current Literature May 23, 2009 Marie-Céline Wipf Group Page 1 of 14 5/27/2009
2 istory of indoles Indole = indigo + oleum, since indole was first isolated by the treatment of the indigo dye with oleum. First prepared synthetically by Adolf von Baeyer in Baeyer, Chem. Ber. 1868, 1, 17 Indigo [] Dioxindole + Zn dust Zn Isatin xindole Indole In 1869, he proposed the formula of indole that is accepted today. Baeyer, Chem. Ber. 1869, 2, 679 Indole derivatives = important dyestuffs until the end of the 19th century. In the 1930s, intensified interest in indole when it was discovered its presence in natural products and bioactive molecules. Marie-Céline Wipf Group Page 2 of 14 5/27/2009
3 Biological importance of indoles Bioactive molecules: tryptophane, tryptamines, auxins 2 L-Tryptophan Essential amino-acid Serotonin eurotransmitter 2 Melatonin eurohormone IAA (indole-3-acetic acid) Phytohormone thers natural alkaloids Ergolines Psychedelic drugs Ergoline β-carbolines CS drugs β-carboline Yohimbans Yohimbine Stimulant drug & aphrodisiac Kr atom alkaloids For some reviews on indole alkaloids, see: Kawasaki and iguchi, at. Prod. Rep. 2005, 22, ; Ishikura and Yamada, at. Prod. Rep. 2009, DI /b820693g St ry chnos nux-vomica alkaloids I boga alkaloids V inca alkaloids Anti-mitotic & anti-microtubule agents Et Et CMe MeC Strychnine Ibogaine CMe Toxic pesticide Psychoactive drug Vinblastine Marie-Céline Wipf Group Page 3 of 14 5/27/2009 Mitragynine Psychostimulant
4 Biological importance of indoles Indole = "privileged structure" Synthetic drugs (orton, Chem. Rev. 2003, 103, ) -> "A single molecular framework able to provide ligands for diverse receptors." (Evans, J. Med. Chem. 1988, 31, ) Indomethacin on-steroidal anti-inflammatory drug Cl Pindolol Beta-blocker Top 200 brand-name drugs in Marie-Céline Wipf Group Page 4 of 14 5/27/2009
5 Methodologies for indole synthesis Sigmatropic rearrangments: Fischer, Gassman, Bartoli, Thyagarajan, Julia Example: Fischer indole synthesis (1883) Fischer, Chem. Ber. 1883, 16, 2241 Buchwald modification (1998) Buchwald, JACS 1998, 120, R Br + Ph Ph 2 Pd BIAP R Ph Ph Ts R 2 R 1 R R 1 R 2 ucleophilic cyclization: Madelung, Schmid, Wender, Couture, Smith, Kihara, enitzescu, Engler, Bailey-Liebeskind, Saegusa Example: Madelung indole synthesis (1912) oulihan modification (1981) R 1 R 1 R 2 nbuli (3 eq.) R 2 Madelung, Chem. Ber. 1912, 45, 1128 oulihan, JC 1981, 46, Marie-Céline Wipf Group Page 5 of 14 5/27/2009
6 Methodologies for indole synthesis Electrophilic cyclization: Bischler, ordlander, Cadogan-Sundberg, Sundberg, emetsberger, Iwao, Magnus, Feldman Example: Bischler-Möhlau indole synthesis (1881) Möhlau, Chem. Ber. 1881, 14, 173; 1882, 15, 2480 Bischler, Chem. Ber. 1892, 25, 2860; 1893, 26, 1336 Reductive cyclization: Reissert, Leimgruber-Batcho, Makosza Example: Leimgruber-Batcho indole synthesis (1973) Me Me 2 2 Ra-i 2 2 xidative cyclization: Watanabe, Knölker Example: Watanabe indole synthesis (1986) R 1 + R 3 R 2 RuCl 2 (PPh 3 ) 3 R 3 R 1 R 2 Batcho and Leimgruber, US Patent , 1973; rg. Synth. 1985, 63, 214 Watanabe, TL 1986, 27, Marie-Céline Wipf Group Page 6 of 14 5/27/2009
7 Methodologies for indole synthesis Radical cyclization: Murphy, Fukuyama Example: Fukuyama indole synthesis (1999) Fukuyama, JACS 1999, 121, Alkyne-based Pd-catalyzed assembly of the indole ring Cycloaddition and electrocyclization: Diels-Alder, photocyclization, Chapman, dipolar cycloaddition Metal-catalyzed indole synthesis: Pd (egedus-mori-eck, Yamanaka-Sakamoto, Larock) Rh, Ru, Ti (Fürstner), Zr, Cr, Mo, Cu (Castro) For a review on indole synthesis, see: Gribble, JCS Perkin Trans. 1, 2000, Pd catalysis: Cacchi, Chem. Rev. 2005, 105, Marie-Céline Wipf Group Page 7 of 14 5/27/2009
8 T.M. catalyzed cyclization with alkynes With ortho-halogenated anilines Limitations: rtho-halogenated anilines required alide byproducts Examples: ne-pot: intermolecular TiCl 4 -catalyzed hydroamination intramolecular Pd(Ac) 2 -catalyzed aza-eck Larock, JACS 1991, 113, Larock, JC 1998, 63, Ackermann, Tetrahedron 2008, 64, Marie-Céline Wipf Group Page 8 of 14 5/27/2009
9 T.M. catalyzed cyclization with alkynes Directing group assisted approach Limitations: Directing group required Examples: ne-pot: InBr 3 -catalyzed enamination of Me acetoacetate Pd(Ac) 2 -catalyzed oxidative cyclization Rh(III)-catalyzed oxydative cyclization with -acetyl anilines Acetyl = directing group Glorius, ACIE 2008, 47, Fagnou, JACS 2008, 130, Marie-Céline Wipf Group Page 9 of 14 5/27/2009
10 T.M. catalyzed cyclization with alkynes Direct approach from simple anilines Challenge Goal of the title paper A unique example: Liu, JC 2006, 71, From anilines and propargyl alcohols: Zn(Tf) 2 -catalyzed C-2 addition of the alcohol Zn(Tf) 2 -catalyzed intramolecular cyclization of the α-amino-ketone intermediate Marie-Céline Wipf Group Page 10 of 14 5/27/2009
11 Title paper: reaction optimization Marie-Céline Wipf Group Page 11 of 14 5/27/2009
12 Title paper: substrates scope Marie-Céline Wipf Group Page 12 of 14 5/27/2009
13 Title paper: reaction applications C 2 Me 3aa C 2 Me 3ua C- activation not reversible: Title paper: mechanistic considerations Proposed mechanism E E Potential intermediate: Intramolecular isotope effect study: Marie-Céline Wipf Group Page 13 of 14 5/27/
14 Title paper: conclusions Direct approach for indole synthesis from simple and readily available anilines and alkynes by C- activation. Unexpensive catalyst. o ligand. o base. 2 used as the oxidant: green chemistry. Limitations: eed high temperature (120 C). Poor investigation of the alkyne substrate scope and R 1 /R 2 regioselectivity. Monosubstitution at position 4 not possible. Scalable? Marie-Céline Wipf Group Page 14 of 14 5/27/2009? 4 3 2
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