Catalytic Reactions for Tri- and Difluoromethylation: The State of Play
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1 Catalytic Reactions for Tri- and Difluoromethylation: The State of Play Véronique Gouverneur University of Oxford Chemistry Research Laboratory BOSS XV Tetrahedron Chair - Lecture 3 July 2016
2 Contents Tri- and Difluoromethylating Reagents Tri- and Difluoromethylation of (Hetero)arenes Csp 3 CF 3 Bond Construction Large Scale Applications
3 Top-Selling Drugs Containing CF 3 [A] [B] [C] [A] US2004/ A1, 2004; [B] Reddy Org. Process Res. Dev. 2007, 11, 842; [C] Lutz J. Med. Chem. 1971, 14, 926.
4 Top-Selling Drugs Containing CF 3 [A] [B] [C] [A] Pierce J. Org. Chem. 1998, 63, 8536; [B] Oh Tetrahedron Lett. 2006, 47, 7943; [C] Ahn Bull. Korean Chem. Soc. 2002, 23, 626.
5 Industrial Preparation of Ar-CF 3 [A] Chlorination of toluene followed by Cl/F exchange [B] Deoxyfluorination of aromatic carboxylic acids [A] Swarts Bull. Acad. R. Belg. 1892, 24, 309; Osswald, Müller, Steinhäuser German Patent, (1933); Filler Adv. Fluorine Chem. 1970, 6, 1; [B] Nickson J. Fluorine Chem. 1991, 55, 173; Hasek, Smith, Engelhardt J. Am. Chem. Soc. 1960, 82, 543.
6 Trifluoromethyl Anion [A] Calculated C-F bond dissociation enthalpy 19 F and 13 C NMR spectra of CF 3 anion [B] Free CF 3 anion [A] Prakash Angew. Chem. Int. Ed. 2014, 53, 11575; [B] Grushin Angew. Chem. Int. Ed. 2015, 54,
7 R = Me: Aldrich, 2400 per mol R = Et: Aldrich, per mol Nucleophilic CF 3 Reagents Prakash Tet. Lett. 1984, 25, 2195 Kashimura J. Org. Chem. 1991, 56, 2 Kobayashi Tet. Lett. 1969, 47, 4095 Paratian J. Chem. Soc., Chem. Commun. 1992, 53 (Phen)CuCF 3 : Aldrich, per mol Burton J. Am. Chem. Soc. 1986, 108, 832 Feng, Weng, Huang Organomet. 2011, 30, 3229 Burton J. Am. Chem. Soc. 1985, 107, 5014 Willis J. Am. Chem. Soc. 1960, 82, 1888 Kondratenko Synthesis 1980, 932 Motherwell Synlett 2002, 646 Langlois Org. Lett. 2000, 2, 2101 Langlois Eur. J. Org. Chem. 2001, 1467 Langlois Tet. Lett. 2003, 44, 1055 Langlois Synlett 2000, 230 Langlois Synlett 2000, 233 Yokoyama Synlett 1996, 1191 Prakash Org. Lett. 2003, 5, 3253 Langlois Matsui Vicic J. Fluorine Chem. 2010, 131, 1108 J. Fluorine Chem. 2007, 128, 1318 Chem. Lett. 1981, 1719 Weng Chem. Eur. J. 2016, 22, 2075 Chen J. Chem. Soc., Perkin Trans. I 1989, 2385 Chen J. Chem. Soc. Chem. Commun. 1989, 705 Palmer US Chen J. Fluorine Chem. 1996, 78, 177 Chen J. Chem. Soc., Chem. Commun Chen Chin. J. Chem. 1994, 464 R = Me: TCI, 2100 per mol Gooβen Chem. Eur. J. 2011, 17, 2689 Colby Org. Lett. 2013, 15, 1208 Burton J. Am. Chem. Soc. 1985, 107, 5014 Xiao Org. Lett. 2015, 17, 532 Umemoto Bull. Chem. Soc. Jpn. 1986, 59, 447 Dolbier Org. Lett. 2001, 3, 4271
8 Properties of CF 3. and CF3+ [A] CH 3 radical vs CF 3 radical [A] Relative rate of reaction with styrene [B] Order of Stability of Fluorinated Radicals [D] Order of Stability of Fluorinated Cations Calculated Stabilisation Energies (ev) [A] Studer Angew. Chem. Int. Ed. 2012, 51, 8950; Dolbier Chem. Rev. 1996, 96, 1557; [B] Jiang J. Org. Chem. 1989, 54, 5648; Pasto J. Org. Chem. 1987, 52, 3062; [C] Beauchamp J. Am. Chem. Soc. 1974, 96, 1269; Viehe Tetrahedron 1987, 43, 4309; Suda Tetrahedron Lett. 1980, 21, 2555.
9 Electrophilic CF 3 Reagents Cheng J. Org. Chem. 2016, 81, 3119; Médebielle J. Fluorine Chem. 2013, 155, 124.
10 Sources of CF 3 Radical Aldrich, 1200 per mol Hazeldine Chem. Commun. 1949, 47, 6632 Akiyama Bull. Chem. Soc. Jpn. 1988, 61, 3531 Szwarc J. Am. Chem. Soc. 1961, 83, 4732 Umemoto Chem. Lett. 1982, 1519 Umemoto Tet. Lett. 1982, 23, 3929 Naumann J. Fluorine Chem. 1985, 30, 73 Naumann J. Fluorine Chem. 1990, 47, 283 Naumann J. Fluorine Chem. 1990, Naumann J. Fluorine Chem. 2000, 106, 217 Umemoto Bull. Chem. Soc. Jpn. 1986, 59, 447 Charles Trans. Faraday Soc. 1960, 56, 794 Muller J. Org. Chem. 1983, 48, 1370 Yoshida J. Chem. Soc. Perkin Trans. I 1989, 909 Sawada J. Fluorine Chem. 1990, 46, 423 Barton Tet. 1986, 42, 2325 Aldrich, 1000 per mol Aldrich, 1200 per mol Kamigata J. Chem. Soc. Perkin Trans. I 1991, 627 Fuchs J. Am. Chem. Soc. 1996, 118, 4486 Langlois Tet. Lett. 2000, 41, 3069 Zard Org. Lett. 2001, 3, 1069 Langlois Phosphorus, Sulfur Silicon Relat. Elem. 1991, 59, 169 Langlois Synlett 2002, 1697 Umemoto Tet. Lett. 1990, 31, 3579 Xiao Chem. Commun. 2011, 47, 6632 Sanford Org. Lett. 2011, 13, 5464 Togni ACS Catal. 2012, 2, 521 Soloshonok Chem. Commun. 2015, 51, 5967 Hu Angew. Chem. Int. Ed. 2016, 55, 2743
11 Adapted from Steiner Chim. Oggi Chem. Today 2015, 33, 26. Routes to CF 3 Reagents
12 Trifluoromethylation of (Hetero)arenes Soloshonok J. Fluorine Chem. 2014, 167, 37; Steiner Chim. Oggi Chem. Today 2015, 33, 26.
13 Palladium Mediated Trifluoromethylation of Aryl Halides Electronic Effects on Reductive Elimination σ* Hartwig Organometallics 2004, 23, 3398.
14 Palladium Mediated Trifluoromethylation of Aryl Halides Effect of Ligands on Reductive Elimination Grushin J. Am. Chem. Soc. 2006, 128, 4632; J. Am. Chem. Soc. 2006, 128, 12644; Ozawa Organometallics 1989, 8, 180.
15 Palladium Catalysed Trifluoromethylation of Aryl Halides Buchwald Science 2010, 328, 1679.
16 Routes to Cu-CF 3 Steiner Chim. Oggi Chem. Today 2015, 33, 26; Normant Tetrahedron 2000, 56, 275.
17 Copper Mediated Trifluoromethylation of Aryl Halides [A] First example [B] First pregenerative route to CuCF 3 [C] First thermally stable and well-defined CuCF 3 complex [A] Kobayashi Tetrahedron Lett. 1969, 47, 4095; J. Chem. Soc., Perkin Trans , 2755; [B] Burton J. Am. Chem. Soc. 1986, 108, 832; [C] Vicic J. Am. Chem. Soc. 2006, 130, 8600.
18 Copper Mediated Trifluoromethylation of Aryl Halides [A] [B] [C] [D] [E] [F] [A] Fuchikami Tetrahedron Lett. 1991, 32, 91; [B] Hartwig Angew. Chem. Int. Ed. 2011, 50, 3793; [C] Chen Tetrahedron Lett. 1991, 32, 7689; [D] Buchwald Angew. Chem. Int. Ed. 2013, 52, 11628; [E] Normant Tetrahedron 2000, 56, 275; [F] Grushin J. Am. Chem. Soc. 2011, 133,
19 Copper Catalysed Trifluoromethylation of Aryl Halides [A] [B] [C] [A] Chen J. Chem. Soc., Chem. Commun. 1989, 705; [B] Amii Chem. Commun. 2009, 1909; [C] Gooßen Chem. Eur. J. 2011, 17, 2689; Novak Org. Lett. 2014, 16, 4268.
20 Copper Mediated Trifluoromethylation of Ar-B(OR) 2 [A] [C] [B] [A] Buchwald J. Org. Chem. 2011, 76, 1174; [B] Gooßen Chem. Eur. J. 2012, 18, 1577; [C] Grushin J. Am. Chem. Soc. 2014, 136,
21 Copper Catalysed Trifluoromethylation of Ar-B(OR) 2 [A] [B] [C] [A] Liu Chem. Comm. 2011, 47, 4300; Shen Org. Lett. 2011, 13, 2342; [B] Sanford J. Am. Chem. Soc. 2012, 134, 9034; [C] Qing J. Org. Chem. 2012, 77, 1251; Beller Chem. Commun. 2013, 49, 2628.
22 Copper Mediated Trifluoromethylation of Diazonium Salts [A] [B] [A] Fu J. Am. Chem. Soc. 2013, 135, 8436; [B] Gooßen Angew. Chem. Int. Ed. 2013, 52, 7972.
23 Copper Mediated Trifluoromethylation of Arylsilanes Hartwig Angew. Chem. Int. Ed. 2016, 55, DOI: /anie
24 Trifluoromethylation via C-H Functionalisation [A] Lewis Acid Activation [B] Palladium Catalysed C-H activation [A] Togni J. Fluorine Chem. 2010, 131, 951; [B] Yu J. Am. Chem. Soc. 2010, 132, 3648; Sanford J. Am. Chem. Soc. 2010, 132, 2878 for recent example using CF 3 Br see: Beller Angew. Chem. Int. Ed. 2016, 55, 2782.
25 Trifluoromethylation via C-H Functionalisation [A] [B] [C] - enhanced reactivity - easily prepared - bench-stable - free-flowing solids [A] MacMillan Nature 2011, 480, 224; [B] Baran Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 14411; [C] Baran Nature 2012, 492, 95.
26 Trifluoromethylation via C-H Functionalisation [A] [B] [A] Ritter Angew. Chem. Int. Ed. 2015, 54, 3712 [B] Li J. Am. Chem. Soc. 2016, 138, 5809.
27 Difluoromethylating Reagents Burton J. Fluorine Chem. 1988, 39, 425 Burton J. Fluorine Chem. 2007, 128, 1198 Prakash Angew. Chem. Int. Ed. 2012, 51, Shen Organomet. 2015, 34, 3065 Baran J. Am. Chem. Soc. 2012, 134, 1494 Chen J. Chem. Soc. Chem. Commun. 1994, 737 Aldrich, 9700 per mol Prakash J. Am. Chem. Soc. 1997, 119, 1572 Prakash Org. Lett. 2007, 9, 1863 Prakash Org. Lett. 2007, 9, 1863 Prakash J. Org. Chem. 2003, 68, 4457 Prakash J. Fluorine Chem. 2011, 132, 792 Akita Chem. Eur. J. 2016, 22, 1262
28 Copper Mediated Aromatic Difluoromethylation of Aryl Halides [A] [B] [C] [A] Amii Org. Lett. 2011, 13, 5560; [B] Hartwig J. Am. Chem. Soc. 2012, 134, 5524; Prakash Angew. Chem. Int. Ed. 2012, 51, 12090; Qing Org. Chem. Front. 2014, 1, 774; [C] Eujen J. Organomet. Chem. 1996, 519, 7; Burton J. Fluorine Chem. 2007, 128, 1198; Vicic J. Am. Chem. Soc. 2016, 138, 2536.
29 Palladium Catalysed Difluoromethylation of Aryl-X and B(OH) 2 [A] [B] [A] Zhang Org. Lett. 2016, 18, 44; [B] Shen Nat. Commun. 2014, 5, 5405.
30 Arene Difluoromethylation via C-H Functionalisation Baran J. Am. Chem. Soc. 2012, 134, 1494.
31 Trifluoromethylation Addition to Carbonyl Groups [A] Pioneering Work [B] Ruppert-Prakash Reagent [A] De Meijere Angew. Chem. Int. Ed. 1977, 16, 854; Angew. Chem. Int. Ed. 1982, 21, 443; [B] Ruppert Tetrahedron Lett. 1984, 25, 2195; Prakash J. Am. Chem. Soc. 1989, 111, 393.
32 Trifluoromethylation Addition to Carbonyl Groups [A] Felkin-Anh [B] Auxiliary Based Methods [C] Chiral Auxiliary Approach [D] Cinchona Alkaloid [A] Pedrosa J. Org. Chem. 2006, 71, 2177; [B] Toru Tetrahedron Lett. 2006, 47, 1337; [C] Prakash Angew. Chem. Int. Ed. 2001, 40, 589; J. Am. Chem. Soc. 2002, 124, 6538; Dolbier J. Org. Chem. 2005, 70, 4741; [D] Shibata J. Fluorine Chem. 2013, 152, 46; Angew. Chem. Int. Ed. 2009, 48, 6324; Feng Tetrahedron 2007, 63, 6822.
33 Trifluoromethylation alpha to Carbonyl Groups [A] [B] [A] Chen Chem. Commun. 1989, 705; [B] Grushin J. Am. Chem. Soc. 2012, 134,
34 Trifluoromethylation alpha to Carbonyl Groups [A] Copper Catalysis [B] Enamine-Copper Catalysis Early works: Umemoto J. Am. Chem. Soc , 2156; Cahard J. Fluorine Chem. 2007, 128, 975; Shibata Org. Biomol. Chem. 2009, 7, 3599; [A] Gade J. Am. Chem. Soc. 2012, 134, 10769; [B] MacMillan J. Am. Chem. Soc. 2010, 132, 4986.
35 Trifluoromethylation alpha to Carbonyl Groups MacMillan J. Am. Chem. Soc. 2009, 131,
36 Allylic Trifluoromethylation of Allyl Halides and Alkenes [A] [B] [C] [D] [A] Nishibayashi Chem. Eur. J. 2012, 18, 13255; Szabo J. Org. Chem. 2013, 78, [B] Qing Org. Lett. 2012, 14, 2106; [C] Liu J. Am. Chem. Soc. 2011, 133, 15300; [D] Buchwald Angew. Chem. Int. Ed. 2011, 50, 9120; Wang J. Am. Chem. Soc. 2011, 133,
37 Trifluoromethylation of Allylsilanes [A] Copper Catalysis [B] Photoredox Catalysis [A] Sodeoka Angew. Chem. Int. Ed. 2012, 51, 4577; Gouverneur Chem. Eur. J. 2012, 18, 8583; [B] Gouverneur Org. Lett. 2013, 15, 1250.
38 Trifluoromethylation of Alkenes [A] [B] Hydrotrifluoromethylation of unactivated alkenes [A] Palacios Chem. Rev. 2015, 115, 1847; Nevado Chem. Soc. Rev. 2014, 43, 6598; [B] Gouverneur J. Am. Chem. Soc. 2013, 135, 2505; Nicewicz Chem. Sci. 2013, 4, 3160; Qing Angew. Chem. Int. Ed. 2013, 52, 2198.
39 Trifluoromethylation of Alkenes Carbotrifluoromethylation [A] [B] Oxytrifluoromethylation [C] [D] Aminotrifluoromethylation [E] [F] [A] Liu J. Am. Chem. Soc. 2014, 136, 10202; [B] Nevado J. Am. Chem. Soc. 2013, 135, 14480; [C] Studer Angew. Chem. Int. Ed. 2012, 51, 8221; [D] Buchwald J. Am. Chem. Soc. 2012, 134, 12462; [E] Akita Org. Lett. 2013, 15, 2136; [F] Liu J. Org. Chem. 2014, 79, 7084.
40 Criteria for Large-Scale Application Criteria + +/- - Substrate cost (generic, based on functional group) Low cost, e.g. Ar-H Ar-Cl Ar-NH 2 Ar-COOH Medium cost, e.g. Ar-Br Ar-Bpin (Pin = pinacolyl) High cost, e.g. Ar-I Ar-B(OH) 2 Reagent Cost Low cost reagent, e.g. HF HCF 3 CF 3 COONa CClF 2 COOMe CF 3 SO 2 Cl Medium cost, e.g. SF 4 CF 3 I TMSCF 3 /TESCF 3 CF 3 SO 2 Na/CF 3 SO 2 K FSO 2 CF 2 COOMe PhCOCF 3 PhSO 2 CF 3 High cost, e.g. Fluolead Togni Reagent Trifluoromethylator Umemoto Reagent Yagupolskii Reagent Cu(P(Ph 3 ) 3 )CF 3 Metal cost Low cost, e.g. Cu, Fe, Sb: s/c > 1 Re, Ru: s/c > 100 Pd: s/c > 1000 Medium cost, e.g. Cu,Sb: s/c = Re, Ru: s/c = Pd: s/c = High cost, e.g. Re, Ru: s/c < 10 Pd: s/c = < 100 Ligand cost Low cost, e.g. 1,10-Phenanthroline: s/c > 10 Brettphos: s/c > 1000 Medium cost, e.g. 1,10-Phenanthroline: s/c = 10 1 Brettphos: s/c = High cost, e.g. 1,10-Phenanthroline: s/c < 1 Brettphos: s/c < 100 Requirement of protocol No special requirement Irradiation Strictly inert conditions Strictly dry conditions Autoclave Secondary containment s/c = substrate to catalyst ratio; Steiner Chim. Oggi Chem. Today 2015, 33, 26.
41 Criteria for Large-Scale Application Criteria + +/- - Toxicity and eco-toxicity of metals and reagents Low e.g. Fe, Zn or metal free HCF 3 Medium e.g. Cu, CF 3 COOR, CF 3 I High e.g. Pd, Ru, HF, SF 4 Metal removal / waste generation Little waste: No metals involved Few reagents, little excess Recyclable solvents Medium waste: Metals (catalytic) Several reagents Recyclable solvents Much waste: Metal (stoichiometric) Several reagents in excess Non-recyclable solvents (i.e. dipolar aprotic solvents) Efficiency and yield of the trifluoromethylbuilding step High efficiency, e.g. Equimolar amounts of reagents Yield: % Moderate efficiency, e.g. Substantial excess of reagents Yield: 60-80% Low efficiency e.g. large excess of reagents Yield < 60% Potential for difficult to remove byproducts (e.g. regioisomers or Ar-H) Very low Low Medium to high Status quo of the trifluoromethylation / fluorination protocol > 100 kg to multi-tonne scale 1 kg to 100 kg scale < 1 kg scale Steiner Chim. Oggi Chem. Today 2015, 33, 26.
42 Potential of Selected Trifluoromethylation Methods Substrate Reagent Cost Metal and Catalyst Cost Specific Requirements Waste Load Toxicity and Eco-toxicity Status Quo Ar-CH 3 Cl 2 (3 eq.) HF (3 eq.) eq. Sb Autoclave HCl Cl 2, HF 100 tonnes Ar-NH 2 Umemoto reagent (1.5 eq.), tbuono 3 eq. Cu - Cu Cu mmol Ar-NH 2 tbuono (1 eq.), ptsa (1.5 eq.) Me 3 SiCF 3 (1.5 eq.) 0.5 eq. CuSCN - Cu Cu mmol Ar-COOH SF 4 (2.5 eq.) HF Autoclave SOF 2 SF 4, HF 100 kg Ar-COOH ArSF 3 (2.5 eq.) - Autoclave ArSOF - mmol Ar-Cl TESCF 3 (2 eq.) 0.05 eq. Pd, Brettphos Strictly dry - Pd mmol Ar-I CClF 2 COOMe (2-4 eq.), KF (1 eq.) eq. CuI - Cu Cu 5 kg Ar-I Ar-Br HCF 3 (1.5 eq.), tbuok, Et 3 N. 3HF 1.5 eq. Cu Strictly inert Cu Cu mmol Ar-I TESCF 3 (2 eq.) 0.1 eq. Cu - Cu Cu mmol Ar-I Trifluoromethylator (1.2 eq.) 1.2 eq. Cu - Cu Cu mmol Ar-B(OH) 2 CF 3 SO 2 Na (3 eq.) (TBHP) 1 eq. Cu - Cu CF 3 SO 2 Na Cu mmol Ar-B(OH) 2 CF 3 I (5 eq.) 0.2 eq. Cu, 0.01 eq. Ru Irradiation Cu, CF 3 I Cu mmol Ar-B(OH) 2 Togni reagent (1.2 eq.) 0.05 eq. Cu, Phen - Cu Cu mmol Ar-Bpin K[B(OMe) 3 CF 3 ] (2 eq.), O 2 1 eq. Cu(OAc) - Cu Cu mmol Het-H CF 3 SO 2 Cl (1-4 eq.) 0.02 eq. Ru, Phen Irradiation Ru mmol Het-H CF 3 I (3 eq.), H 2 O 2 (2 eq.) 0.3 eq. FeSO 4 or Cp 2 Fe - CF 3 I CF 3 I 40 kg Het-H Zn(CF 3 SO 2 ) 2 (1-4 eq.) TBHP (3-5 eq.) Zn - Zn Zn mmol Steiner Chim. Oggi Chem. Today 2015, 33, 26.
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