Cu- Catalyzed Synthesis of Diaryl Thioethers and S- Cycles by reaction of Aryl Iodides with Carbon Disul;ide in the Presence of DBU.
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1 Cu- Catalyzed ynthesis of Diaryl Thioethers and - Cycles by reaction of Aryl odides with Carbon Disul;ide in the Presence of DBU. Peng Zhao, Hang Yin, Hongxin, Gao, Chanjuan Xi.; J. rg. Chem. ArCcle AAP D: /jo400709s James Johnson Current Literature 5/11/2013
2 Diarylthioethers Diarylthioethers have shown accvity against cancer, HV, Alzheimer s disease, inflammacon, and asthma. ElectronegaCvity and Bonding xygen 3.44 ulfur 2.58 N Ar AZD A Ar Ar H 5c N H 1.75A Ar The image cannot be displayed. Your computer may not have enough memory to open the image, or the image may have been corrupted. estart your computer, and then open the file again. f the red x still appears, you may have to delete the image and then insert it again. 2 Molecules 2011, 16, Top rganomet Chem (2010) 31: Tetrahedron 1984, 40, 1433.
3 Palladium Catalyzed - Arylation - 8 mol% Pd(PPh 3 ) 4 H, 3h, reflux 36-93% 15 examples X -H X=Br, Cl Cl Ar-H Ar-H 2 mol% Pd(Ac) 2 DiPPF, t-buna dioxane 18h, 100 C 70-90% 8 examples 2 mol% Pd Josiphos, t-buna Toluene, 110 C 70-99% 11 examples 2 mol% Pd/C KH DM, 110 C 65-99% 14 examples Ar Ar 3 Bull. Chem. oc. Jpn. 1980, 53, JC. 2004, 69, Chem. Eur. J. 2006, 12, Adv. ynth. Catal. 2009, 351,
4 Cu Catalyzed - Arylation X H K 2 C 3 X=, Br, Cl, F DMF, 135 C 24h Br 1) nbuli, -78 C, THF 2) 8 B(H) 2 Tet Lec 39 (1998) J. rg. Chem. 2004, 69, J. rg. Chem. 2012, 77, J. rg. Chem. 2008, 73, H Ar-H -H 3) X 71-96% 17 examples Cu(Ac) 2 (1.5 eq) pyridine 4A M, DMF 40-90% 2.5 mol% Cu K 2 C 3 2eq NMP, 6 h, 100 C 46-96% 8 examples 5 mol% Cu 2 eq. HCH 2 CH 2 H 2 eq. K 2 C 3 iprh,18-22h, 80 C 82-93% 10 examples Ar = Ar, Alkyl 4
5 -H Cu Catalyzed - Arylation Cu 10 mol% 10 mol% tripod ligand Cs 2 C 3 DMF: dioxane(1:9) 24h, 110 C H H Cu H Ar-H 10 mol% CuBr Ligand, Cs 2 C 3 DM, 24h, 60 C Ar L B(H) 2 H H B(H) 2 N 5 mol% Cu 4 1, 10-Phen.H 2 (5 mol%) nbu 4 NH(40%aq.) H, rt, 8h, % 50 examples Cu 10 mol% Neocuproine 10 mol% 1.5eq. Nat-Bu Toluene, 110 C 81-97% 16 examples CuMeal (20-30 mol%) THF, C 2-12h 56-83% 13 examples N N 1, 10-Phen. N N Neocuproine H Meal 5 rg. Lec., 2002, 4,. 20, 3517 rg. Lec., 2002l. 4,. 16,
6 ther Metal Catalyzed - arylation X X=, Br -H 1 mol% Co 2 (dppe) Zn (1.5eq), pyr CH 3 CN, 10h, 80 C 29-98% 22 examples Ar-H Ar-H Ar-H 10 mol% FeCl 3 20 mol% DMEDA NatBu Toluene, 24h, 135 C 10 mol% FeCl 3 10 mol% BNAP NatBu Toluene, 24h, 135 C [(Pr)Ni(allyl)Cl] Nat-Bu DMF, 24h, 100 C Ar Ar Ar 33-98% 18 examples 72-95% 12 examples 76-99% 13 examples 6 rg. Lec., Vol. 8, No. 24, 2006 Chem. Commun., 2009, Angew. Chem. nt. Ed. 2008, 47, rg. Le=. 2007, 9,
7 s it Fe or Cu? 7 Angew. Chem. nt. Ed. 2009, 48,
8 Nanoparticles -H 3 mol% Cu np KH 1.5 eq. DM, 24h, 135 C 88-99% 7 examples -H -H 1 mol% Cu on mseoporous i 2 Cs 2 C 3 dioxane, 21h, 110 C 3 mol% n 2 3 np KH 2 eq. DM, 24h, 135 C 65-96% 24 examples 56-97% 15 examples recyclable catalyst 8 Angew. Chem., nt. Ed. 2007, 46, Chem. Commun. 2010, 46, 282. rg. Lec. 2009, 11, 1697.
9 Previous work 9 rg. Lec., 2010, 12, 17, 3930
10 Title Paper 10 D: /jo400709s
11 ptimization 11 D: /jo400709s
12 Catalytic Cycle 12 J. Acta Crystallogr. 1986, C42, 487. Published in: Peng Zhao; Hang Yin; Hongxin Gao; Chanjuan Xi; J. rg. Chem. ArCcle AAP D: /jo400709s
13 10 mol% Cu DBU, C 2 Toluene, 100 C 12h Yield Yield Yield Yield H 85% 2- NMe 2 78% 2- Me 83% 4- Ph 56% 4- Me 80% 2- H 81% 2- Me 75% 2,4- Me 70% 3- Me 65% 4- Me 68% 2- Br 65% 2,5- Me 68% 4- Br 74% 3- C 2 Me 65% 4- C 2 Me 65% 2,4,6- Me 50% 4- Cl 70% 4- CF 3 78% 1- Nap 84% 4- Pyr 75% 2- Pyr 66% 2- Thiophene 70% 13
14 ntramolecular C- - C formation Ar Ar 10 mol% Cu DBU, C 2 Toluene, 100 C 12h Ar Ar N H H 75% N 62% 65% Bu Ph 74% Bu 68% 78% Ph 14 72%
15 Conclusions ntramolecular coupling of two aryl iodides to form a diaryl thioether. FuncConal group tolerant. Cu $.23/g, Pd(Ac) 2 $94/g, FeCl 3 $.26/g Homocoupling applicacon C 2 inexpensive and easy to use 15 Alfa Aesear Top rganomet Chem (2010) 31: Tetrahedron 1984, 40, 1433.
16 Previous work: 16 JC. 2012, 77, rg. Lec., 2010, 12, 17, 3930 Tet Lec 54 (2013)
17 Previous work: 17 JC. 2012, 77, rg. Lec., 2010, 12, 17, 3930 Tet Lec 54 (2013)
18 Palladium catalytic cycle 18
19 Chan Lam Catalytic cycle 19
20 Cobalt Catalyzed 20
21 21 Published in: Peng Zhao; Hang Yin; Hongxin Gao; Chanjuan Xi; J. rg. Chem. ArCcle AAP D: /jo400709s Copyright 2013 American Chemical ociety
22 22 J. Med. Chem. 2005, 48,
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