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1 Vol. 9, o. 5 Gold Chemistry Features include: Gold complex used in various transformations with alkynes and alkenes
2 2 Introduction Introduction Bond 1 C 2 utchings ashmi Echavarren olan Toste William Sommer roduct Manager eferences: (1) Bond, G. C. et al. J. Chem. Soc. Chem. Commun. 1973, 444. (2) aruta, M. et al. Chem. Lett. 1987, 16, 405. (3) utchings, G. J. J. Catal. 1985, 96, 292. (4) ashmi, A. S. K. J. rganomet. Chem. 2009, 694, CAS MSDS M, I aman, UV DF sigma-aldrich.com/japan My rofile 1) Web language=japanese, 2) MSDS=English, 3) Country=Japan 3 Submit Web Tel: Fax: sialjpts@sial.com
3 3 Thomas ,3 π Figure 1 2 Figure 1 u + u - L ' L L ' u L u 4 C C a 4 Scheme Scheme 1 ' a(4) C3C, 79 C C3 ' 64-92% ( mol %) 3W1240 ( mol %) Br 70 C 1 2 Br ucleophilic Addition to Alkynes C mol 99 Scheme Dake Scheme 3 7 Dake 2006 Crawley Funk B 8 7-exo-dig Scheme 4 40 C 2 2 AgTf 3 89 Scheme 2 Scheme 3 Scheme 4 98% 94% 93% 96% AgTf C 79% 38% AgTf, C22 40 C, 12h (2.5 mol %) AgSbF6, C 2 2, 35 C 89% 1 2 Schmidt Toste Schmidt 9 Scheme mol Scheme 5 82% 78% F 93% F F 61% Tel: Fax: safcjp@sial.com
4 4 ucleophilic Addition to Alkynes sigma-aldrich.com/japan 2005 Toste 10 5 mol 3 5 mol AgSBF 6 Scheme 6 Johansson mol -DTBM-SEGS 2 5 mol AgSbF 6 Scheme 7 cis trans ee Toste III 11 Shapiro Toste α,β- Scheme 8 - β ,4-1,5-1,6-1, Toste 1, AgBF 4 AgF 6 AgSbF mol Scheme 9 Toste 2005 autenstrauch 1, SbF 6 3 Tf Scheme Scheme 6 Tel: Fax: iv Scheme 7 Bz Scheme 8 Scheme % (6:1) 3C C3 iv + + iv 70%, 81% ee Ar iv 61% (>20:1) F Ar + Bz AgSbF6 Me 2, rt sialjpts@sial.com Ac 69% (1.2:1) C3 2 2 C3 (2.5 mol %) AgSbF6 Me2, rt >20:1 cis:trans iv 85%, 82% ee C2 2, rt 87% 88% C3 65% Bz TIS Bz F6 (3 mol %) C 2 2, rt SbF 6 (1 mol %) C22, rt 3C 62% Bz 3C C3 Ar Ar 1 Bz 73% iv 71%, 94% ee Bz C3 80% 99%, 91% ee, >99:1 dr 94% iv Bz TIS
5 5 5 mol I Echavarren 1,6-14 Scheme 11 1 iv 2 84%, 82% ee SbF6 C3C, - 20 C, 12 h 80%, 77% ee %, 96% ee Zou Scheme 12 Zou 89 ee 1, Echavarren 4+2 pycnantuquinones A Echavarren Johnos Scheme 13 anti syn Scheme 10 Scheme 11 Scheme 12 CC3 (3 mol %) C22, rt SbF6 29% 52% 39% Ac C 22, rt, then Me K 2C 3 (2 eq.) 72% ucleophilic Addition to Alkynes SbF6 CC 3 3C2C 3C2C 3 (2 mol %) C22, rt 3C2C 3C2C C2C 3C2C 1 3 3C2C 3C2C C 3C2C 3C2C 2 78% 74% 58% 3 AgSbF 6 C22, rt 2S 2S Scheme 13 94% 56% Tel: Fax: safcjp@sial.com
6 6 ucleophilic Addition to Alkynes 100 olan 17 olan - C -C 1,4- Scheme ppm eferences: (1) orman,.. C. et al. J. Chem. Soc. erkin Trans , (2) (a) ashmi, A. S. K. Chem. ev. 2007, 107, (b) Jiménez-úñez, E. et al. Chem. Commun. 2007, 333. (c) ashmi, A. S. K. Angew. Chem., Int. Ed. 2006, 45, (3) ashmi, A. S. K. Gold Bull. 2003, 36, 3. (4) Widenhoefer,. A. et al. Eur. J. rg. Chem. 2006, (5) Fukuda, Y. et al. Synthesis 1991, 975. (6) Mizushima, E. et al. rg. Lett. 2003, 5, (7) arrison, T. J. et al. J. rg. Chem. 2006, 71, (8) Crawley, S. L.; Funk,. L. rg. Lett. 2006, 8, (9) Gorin, D. J. et al. J. Am. Chem. Soc. 2005, 127, (10) Johansson, M. J. et al. J. Am. Chem. Soc. 2005, 127, (11) Shapiro,. D. et al. J. Am. Chem. Soc. 2008, 130, (12) Luzung, M.. et al. J. Am. Chem. Soc. 2004, 126, (13) Shi, X. et al. J. Am. Chem. Soc. 2005, 127, (14) Jiménez-úñez, E. et al. Angew. Chem., Int. Ed. 2006, 45, (15) Zou, Y. et al. Angew. Chem., Int. Ed. 2008, 47, (16) ieto-berhuber, C. et al. J. Am. Chem. Soc. 2008, 130, 269. (17) Marion,. et al. J. Am. Chem. Soc. 2009, 131, 448. Scheme 14 3C 1 2 (0.01 mol %) AgSbF6 1,4-dioxane/2 (2:1) 120 C, 18 h F % 97% 72% 76% 95% ew Buchwald alladacycles C d d 0 d 0 d 2 dba 3 d II d Buchwald d Et2C EWG 86% 2 + C3 C 99% mol% K2C3,, 1 h, 110 C C3 C3 2 d Cy 2 EWG C 2 90% 97% (with ) n-bu sigma-aldrich.com/japan 2 d Cy (from Xos) sigma-aldrich.com 2 d Cy (from Sphos) 2 d Cy (from uos) Tel: Fax: d (from Xos) sialjpts@sial.com
7 7 1,2-3 1 Toste mol 6 mol AgBF 4 Scheme 1 Toste mol 5 mol AgSbF 6 Scheme 2 trans 2007 Toste 4 LaLonde Scheme mol Scheme 1 Scheme 2 X 3C 2C 3C2C 92%, 95% ee X 2S 2S 89% C C 3 (3 mol %) AgBF4 (6 mol %) C22, 4 C 3C2C 3C2C 86%, 95% ee 3 AgSbF6 C22, rt Ts 83% C3 2 2 X X 3C 2C 3C2C 83%, 95% ee 81% ucleophilic Additions to Allenes C 3 ' ' Ts (3 mol %) DCE, rt ' ' Ts Ts Ts Ts Ts 98%, 99% ee 90%, 99% ee 75%, 83% ee 88%, 98% ee Scheme 3 Tel: Fax: safcjp@sial.com
8 Buzas 1, Diels-Alder 4+1 Xos- Buzas 1 mol 100Scheme 4 iv Tf2 (Cy)2 (1 mol %) C22, rt Ac Bz Bz n-c511 ropargyl aisen earrangement eferences: (1) ashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 2000, 39, (2) Luzung, M.. et al. J. Am. Chem. Soc. 2007, 129, (3) Mauleón,. et al. J. Am. Chem. Soc. 2009, 131, (4) LaLonde,. L. et al. J. Am. Chem. Soc. 2007, 129, (5) Buzas, A. K. et al. rg. Lett. 2007, 9, 985. aisen 2004 Toste 3 3 BF 4 aisen 1 mol Scheme 1 100% Scheme % BF (1 mol %) C22, rt; ab4, Me, rt iv 99% % eference: Sherry, B. D. et al. J. Am. Chem. Soc. 2004, 126, F 3C 78% 81% 86% Scheme 1 Got Chemews? Aldrich Chemews sigma-aldrich.com/japan sigma-aldrich.com Tel: Fax: sialjpts@sial.com
9 9 Gold Complexes (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate [ ] C C3 C F 6 Sb FW SbF MG 250 mg 14, G 1 g 53,100 Bis(chlorogold(I)) bis(diphenylphosphino)methane, 97% C FW MG 250 mg 11, G 1 g 36,400 [Bis(trifluoromethanesulfonyl)imidate](triphenylphosphine) gold(i) (2:1) tolu ene adduct C F S 4 FW F3C S S CF3 1 /2 C3C MG 250 mg 13, G 1 g 42,200 Chloro[(1,1 -biphenyl-2-yl)di-tert-butylphosphine]gold(i), 98% [ ] C FW MG 250 mg 11, G 1 g 32,100 Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) [ ] C FW MG 100 mg 6, MG 500 mg 21,900 Chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] gold(i), 95% C C3 FW MG 100 mg 6, MG 500 mg 23,800 3C Chloro[2-dicyclohexyl(2,4,6 -trisopropylbiphenyl) phosphine]gold(i) [ ] C FW C 3 3C 3C C3 Chloro(dimethylphenylphosphine)gold, 97% [ ] C 8 11 FW C3 C MG 250 mg 11, G 1 g 33,000 Chloro(methyldiphenylphosphine)gold(I) [ ] C FW C Inquire Chloro(tri-tert-butylphosphine)gold(I) [ ] C FW MG 250 mg 13, G 1 g 40,000 Chloro(triethylphosphine)gold(I), 97% [ ] C 6 15 FW MG 250 mg 9, G 1 g 26,100 Chloro(trimethylphosphine)gold(I), 99% [ ] C 3 9 C3 3C FW C MG 250 mg 20, G 1 g 61,500 Chloro(tri phenyl phos phine)gold(i), 99.9% trace metals basis [ ] C FW MG 500 mg 26, G 5 g 101,100 Chloro(triphenylphosphite)gold, 97% C FW C 3C MG 250 mg 7, G 1 g 21,200 Chloro[tris(2,4-di-tert-butylphenyl)phosphite]gold [ ] C FW t Bu t Bu MG 500 mg 7,500 t Bu t Bu t Bu C3 t Bu Gold Complexes MG 250 mg 10, G 1 g 29,400 Tel: Fax: safcjp@sial.com
10 10 Chloro[tris(para-trifluoromethylphenyl)phosphine]gold(I), 99% [ ] C F 9 FW F 3C CF 3 ()-DTBM-SEG S () 2 C FW C3 C 3 Gold Complexes sigma-aldrich.com/japan MG 250 mg 14, G 1 g 47,900 Chloro[tri(o-tolyl)phosphine]gold(I) [ ] C FW Tel: Fax: CF3 C 3 3C C MG 500 mg 17,000 Chloro[tri(p-tolyl)phosphine]gold(I) [ ] C FW MG 500 mg 15,000 Dichloro[(±) BIA]digold(I) [ ] C FW C C3 C MG 250 mg 10,000 Dichloro(DE)digold(I) [ ] C FW MG 250 mg 13,800 Dichloro(2-pyridinecarboxylato)gold [ ] C FW G 1 g 5, G 5 g 14,600 2-Dicyclo hexyl phos phino-2,4,6 -triisopropylbiphenyl gold(i) bis(trifluoromethanesulfonyl)imide [ ] C F 6 4 S 2 FW CF3 S S CF MG 250 mg 15, G 1 g 43,700 sialjpts@sial.com C3 C MG 100 mg 24,000 Gold(III) bro mide hydrate, 99.9% trace metals basis [ ] Br3 Br 3 x 2 FW (Anh) G 1 g 19, G 5 g 65,500 Gold(I) chloride, 99.9% trace metals basis [ ] FW G 1 g 28, G 5 g 114,800 Gold(III) chloride, 99.99% trace metals basis [ ] 3 3 FW MG 250 mg 10, G 1 g 34,700 Gold(III) chloride trihydrate, 49.0% basis [ ] FW G4022-1G 1 g 10,100 G4022-5G 5 g 40,900 G G 10 g 67,900 G G 25 g 147,400 Methyl(tri phenyl phos phine)gold(i) [ ] C FW MG 500 mg 23,000 Sodium tetra chloro aurate(iii) dihydrate, 99% [ ] a a 2 2 FW G 1 g 12, G 5 g 67,400 Trichloro(pyridine)gold(III), 97% [ ] 3 C FW MG 250 mg 13, MG 500 mg 22, G 1 g 40,300 Tris(triphenylphosphinegold)oxonium tetrafluoroborate [ ] C BF 4 FW BF MG 250 mg 10, G 1 g 31,900
11 11 Silver Salts Additives Silver bis(trifluoromethanesulfonyl)imide, 97% C 2 AgF 6 4 S 2 FW Ag CF3 S S CF MG 500 mg 14, G 5 g 95,300 Silver hexafluorophosphate, 98% [ ] AgF6 AgF 6 FW G 1 g 8, G 10 g 49,100 Silver methanesulfonate [ ] C 3 Ag 3 S FW C S G 5 g 7, G 25 g 27,200 Silver perchlorate, 97% [ ] Ag 4 Ag 4 FW G 5 g 10, G 25 g 31,100 Ag + Silver tetrafluoroborate, 98% [ ] AgBF4 AgBF 4 FW G 1 g 4, G 10 g 19, G 50 g 65,000 Silver p-toluenesulfonate, 99% [ ] C 7 7 Ag 3 S FW C S Ag G 10 g 14, G 25 g 26,400 Silver trifluoroacetate, 98% [ ] C 2 AgF 3 2 FW F3C Ag T G 5 g 8,000 T G 25 g 31,700 Silver trifluoromethanesulfonate, 99% [ ] CAgF 3 3 S FW F3C S Ag G 1 g 3, G 10 g 14, G 25 g 25,100 Silver Salts Additives Continuing the Tradition of Excellence Sigma-Aldrich s highly acclaimed chemistry review journal, Aldrichimica Acta, has again been ranked #1 (out of 55 similar journals) by Impact Factor in the field of rganic Chemistry. Aldrichimica Acta Growing Impact over the ast Six Years * To get your FEE subscription to the Aldrichimica Acta, please visit our award-winning Web site at sigma-aldrich.com/acta Impact Factor Year *Impact Factor data published by Thomson euters Journal Citation eports. sigma-aldrich.com Tel: Fax: safcjp@sial.com
12 Chem roduct Central Substructure Search Building Blocks rganic Building Blocks eterocyclic Building Blocks Amino Acid Derivatives Unnatural Amino Acid Derivatives Monosaccharides ucleosides Chiral Building Blocks rganometallic eagents Boronic Acids and Derivatives Grignard eagents ieke and rganozinc eagents rganolithium rganosilicon rganotin rganoaluminum thers Synthetic eagents Coupling Lewis Acids C-C Bond Formation rganic Acids C-X Bond Formation (alogen) Inorganic Acids C-X Bond Formation (onhalogen) osphazene Bases rganic Bases xidation Inorganic Bases eduction Inorganic Salts rotection and Derivatization Dehydrating eagents adical Chemistry Compressed and ase Transfer Catalysts Liquified Gases Chelation/Complexation Compounds Asymmetric Synthesis Chiral Catalysts, Ligands, and eagents Chiral xiliaries Chiral Building Blocks Chiral esolution eagents Ionic Liquids Ammonium Choline Imidazolium osphonium yrazolium yridinium yrrolidinium Sulfonium Specialty Synthesis igh Throughput Synthesis Chemical Ligation eptide Synthesis Carbohydrate Synthesis ligonucleotide Synthesis Enzyme-Mediated Synthesis Fluorous Synthesis Supported Synthesis
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