Catalytic Reactions in Organic Synthesis
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1 17 April, 2008 Catalytic eactions in rganic Synthesis hodium Complexes and edox Catalysts Koichi AASAKA, Motoki YAMAE, Shunsuke CIBA Division of Chemistry and Biological Chemistry, School of ysical and Mathematical Sciences
2 hodium Complexes Electron Deficient-Lower Valent h Complexes Bimetallic h Complexes edox Catalysts tal Catalyzed ne-electron Transfer rganic Electron Transfer eagents Bronsted & Lewis Acids and Bases tal Catalysts for Coupling, Addition, etc. rgano-catalysts Biocatalysts
3 Et 2 C Et 2 C Et C (C) 2 h Cl Cl h(c) 2 Et 2 C Et 2 C Et Catalytic Intramolecular Pauson Khand eactions (~1997) Catalyst Solvent C / atm Temp. / C Jeong and Chung 2 mol% Co(cod)(indenyl) DME Jeong and Chung 3 mol% Co 2 (C) 8 / P() 3 DME Co Chung 5 mol% Co(acac) 2 / ab 4 C 2 Cl Jeong mol% Co 2 (C) 8 scc Chung 1 mol% Co 4 (C) 12 C 2 Cl Livinghouse 5 mol% Co 2 (C) 8 / hν DME Ti u Buchwald 5-20 mol% CpTi(C) 2 Toluene 1 90 Chung 5-20 mol% (chiral Cp)Ti(C) 2 Toluene 1 90 Murai 2 mol% u 3 (C) 12 dioxane Mitsudo 2 mol% u 3 (C) 12 DMAc
4 Et 2 C Et 2 C Et 1mol%[hCl(C) 2 ] 2 C Ar dibutyl ether, 130 C Et 2 C Et 2 C Et pressure / atm C Ar time / h yield / % (recovery / %) trace (ca. 100) (24) 1.0 Consumption Curves of the Starting Material atm C 1 atm C / h half life 1 atm C 6.4 h 0.1 atm C 0.5 h
5 5 mol% [hcl(c) 2 ] 2 Et 2 C C (0.1 atm), Ar (0.9 atm) Et 2 C Et 2 C Et 80 C, toluene, 18 h, 1 M 2 C (cis : trans = 23 : 77 ) 93% (cis : trans = 22 : 78 ) Et 2 C Et 2 C 5 mol% [hcl(c) 2 ] 2 C (1 atm) dibutyl ether, 160 C, 5 h Et 2 C Et 2 C 93% 5 mol% [hcl(c) 2 ] 2 C (0.1 atm), Ar (0.9 atm) toluene, 0.1 M, 60 C, 30 h 91% J. rganomet. Chem. 2001, 624, 73.
6 Activation of Acyl and Vinyl Silanes with [hcl(c) 2 ] 2 Si Si 3 3 stable & isolable organometallic compounds Si 2 F X X =, alogen: unstable hcl 3 igh xidation State h 2 ( 2 CC 3 ) 4 Electron Deficient h Electron ich C C h Cl C h Cl C Low xidation State Cl 3 P h P 3 P 3
7 2 Si Si 2 2 C C 2 3 mol% Pd(P 3 ) 4 benzene, reflux 2 Si 2 C Si 2 C 2 85% Pd(0) oxidative addition Pd(0) 3 Si II Pd L n Si 3 C 3 Si II Pd Si 3 L n 3 Si II 2 C C 2 3 Si Pd L n 2 C C 2 2 Si Si 2 3 mol% Pd(P 3 ) 4 benzene, reflux 2 Si Si 2 85% Chem. Lett., 1996, 841.
8 Acylsilanes (Air Stable Acyl Main Group tal Compounds) (2001 ) M 1 2 Si 3 Si 3? M Si 3? 1 2 Si 2 5 mol% Pd (P 3 ) 4 toluene, 100 C, 14 h Si 2 Acylsilane ecovery 10% 90% Si 2 5 mol% [ h Cl(C) 2 ] 2 toluene, 100 C, 5 h Acylsilane ecovery 11% 37%
9 Si 3 ' 5 mol% [hcl(c) 2 ] 2 C 3 C 2 (10 mol.amt.) toluene ' ' Si 3 temp. time yield Si 2 70 C 12 h 82% 100 C 5 h 80% (C 2 ) 2 Si 2 70 C 12 h 77% Si 3 70 C 24 h 77% Si C 3 h 81% Chem. Lett. 2001, Si 2 5 mol% [hcl(c) 2 ] 2 C 3 C 2 (10 mol.amt.) toluene, 70 C, 12 h = : = C 3 7 : 52% 44% 1/2 [hcl(c) 2 ] 2 C 3 C 2 toluene-d 8, 80 C, 5 h o eaction
10 oxidative addition III Cl h Si 2 Cl III h Si 2 h I Si 2? h I X Si 2 metal exchange ClSi 2 ClSi 2 h I ClSi 2 h I C 3 C 2 h I (C 2 5 C) 2 EtC III h CC 2 5 CEt (or Et) h I
11 Acylsilane or Vinylsilane? Si 3 keto form Si 3 hcl h(cl)si 3 h(i) Si 3 enol form Si 3 hcl h(cl)si 3 pka C 3 = Si 3 = C i-c A. J. Kresge, J. B. Tobin J. Am. Chem. Soc. 1990, 112, 2805.
12 Si 2 1) i-pr 2 Li / TF 78-0 ÞC 2) I, TF 0 ÞC - rt Si 2 keto form 82% ( 3 : 2 ) Si 2 pseudo enol form Si 2 Si 2 hi or III keto form 3 : 2 pseudo enol form 5 mol% [hcl(c) 2 ] 2, C 3 C 2 Toluene, 100 ÞC, 12 h hi or III 73% 33% besed on keto form based on pseudo enol form
13 Catalytic Acylation of Vinylsilanes Si' 3 hx < metal exchange > X Si' 3 < reductive elimination > h h C < oxidative addition > Stoichiometric eaction Si 2 1/2 [hcl(c) 2 ] 2 Toluene-d 8 h(c) n 80 C, 10 h Cl Si 2 Si 2 (Si 2 ) 2 monitored by 1 M (s, C 3 ) 38% (δ 0.43) 9% (δ 0.23) 33% (δ 0.31)
14 Catalytic Acylation of Vinylsilanes with acid anhydrides Si 2 (C 2 ) 2 with carboxylic acids 5 mol% [hcl(c) 2 ] 2 1,4-Dioxane, 90 C, 6 h (C 2) 2 76% (C 2 ) 2 Si 2 5 mol% [hcl(c) 2 ] 2 (t-buc) 2 1,4-Dioxane, 90 C (C 2 ) 2 (C 2 ) 2 8 h 75% (C 2 ) 2 C 3 12 h 66% (C 2 ) 2 12 h 65%
15 Preparation of Unsymmetrical α-diketones Si (C 2 ) 3 2 C (C 2 ) 2 C 3 (C 3 C) 2 K 2 C 3, rt 5-15 min 5 mol% [hcl(c) 2 ] 2 Toluene, 80 C (C 2 ) 2 (C 2 ) 2 C 3 99% C 3 92% (C 2 ) 2 C 3 CF 3 C 2 C 2 Cl 2, rt (C 2 ) 2 C 3 quant.
16 etroatom-bridged Bimetallic Complexes h X h 2 P X P 2 h h Cl 4 X =, X = S W X h 2 P L(C) 4 W h(p 3 )(C) P. M. Shulman et al, rganometallics, 1987, 6, 101.
17 ydroformylation of Alkenes Catalyst C / 2 C aldehyde alkenes alkane (Et 2 P)(C) 4 W 2 P h (P 3 )(C) I C C C W C C C 2 cat. Pd(Ac) 2 DBU TF, 100 C, 15 min microwaves 77%. F. K. Kaiser, A. allberg, K. Larhed, J. Comb. Chem. 2002, 4, 109.
18 20 mol% Catalyst C / 2 (1 atm) Toluene, rt, 20 h aldehyde C alkenes alkane 2 P (Et 2 P)(C) 4 W h(p 3 )(C) h(c)(p 3 ) 3 Yield / % Yield / % C Pressure / atm C Pressure / atm
19 20 mol% Catalyst C / 2 (1 atm) (C 2 ) 2 Toluene, rt, 36 h C C C (C 2 ) 2 (C 2 ) 2 (C 2 ) 2 (C 2 ) 2 monoaldehyde dial alkenes alkane 2 P (Et 2 P)(C) 4 W h(p 3 )(C) h(c)(p 3 ) 3 monoaldehyde dial alkenes alkane 89% (n : iso = 2.5 : 1) 0% 4% 0% 60% (n : iso = 2.5 : 1) <12% 14% 10%
20 edox-catalysts for Generation of adical Species present X X Y Y Y Y Y Y Y Y Products
21 Generation of β-keto adicals: Intermolecular Addition to lefins SiBu t 2 Mn( 2 CPy) 3 S SiBu t 2 SiBu t 2 S Mn( 2 CPy) 3 S 70% S Mn( 2 CPy) 3 = Chem. Lett., 1993, 545. C 2 Mn 3 excess Cu( 3 ) 2 C, 3 C 43% S. E. Schaafsma et al., Tetrahedron Lett., 1973, 827.
22 Si 2 t-bu C Mn 3 ( Mn( 2 CPy) 3 ) DMF, 0 C 81% purity > 90% Si 2 t-bu Mn( 2 CPy) 3 Mn( 2 CPy) Mn( 2 CPy) n-bu 3 Sn DMF, 0 C C 3 75% Chem. Lett., 1994, 1697.
23 C C 2 sordarin Synthesis of ( )-Sordarin Synthesis of ( )-Sordarin: see J. Am. Chem.Soc., 128, 6931 (2006). X C sordaricin D. auser, et al., elv. Chim. Acta, 54,1178 (1971). selective inhibitor of fungal protein synthesis: M. C. Justice, et al., J. Biol. Chem., 273, 3148 (1998). β(1,2-cis) C 2 C 2 Et C C 2 C 2 Et C 2 Et C 2 Et Et
24 Preparation of Bicyclo[5.3.0]decan-3-one Derivative TBS Mn( 2 CPy) 3, DMF, 0 C 92% TBS C C 2 TBS = t-bu 2 Si Mn( 2 CPy) 3 = TBS TBS TBS Mn 2 C 3 n-bu 3 Sn, Mn(pic) 3 TP DMF, 0 C, 1 h 86% TP Bull. Chem. Soc. Jpn., 72, 85 (1999).
25 Ag(I)-Pyridine Catalytic System Si(t-Bu) 2 Ag(I) ( 4 ) 2 S 2 8 Ag(0) 0.1 mol amt. Ag mol amt. pyridine 2.4 mol amt. ( 4 ) 2 S 2 8 DMF, rt 86% TBSX 3 or 1/ 2 2 S 4 ( 4 ) 2 S 2 8 β-keto radical TBS 3 TBS Ag(I) Ag(0) 3 TBS Chem. Lett., 35, 18 (2006).
26 C 2 d-( )-quinic acid a) 1) MgBr CuBr S 2, 3 SiCl TF MPA, 91% 2) Et 2 Zn, C 2 I 2, Et 2 TBS 3) K 2 C 3, 81% (2 steps) > 99.8% ee 24 [α] D = (c = 1.06, CCl 3 ) 10 mol% Ag mol amt. pyridine 2.4 mol amt. ( 4 ) 2 S mol amt. TBS DMF, 20 ~ 25 C, 4h 85% TBS a) C. D. Maycock, et al., J. Chem. Soc., Perkin Trans. I, 2001, 166.
27 Y e Y Y Anion adical of xime Alkylidne Aminyl adical S S hv C 2 Cl 2, rt SCS 77% F. Gagosz and S. Z. Zard, Synlett, 1999, SCl S SS S C 2 Cl 2, -50 ~0 ÞC 70% S. M. Weinreb et al., rg. Lett., 1, 637 (1999).
28 2 2 excess a, radical trapping reagent 2 2 1,4-dioxane 50 C, 6-10 h Y 91% (Y = ) 2 2 CCl 4 SS SeSe 75% 70% 69% (Y = Cl) (Y= S) (Y = Se) Chem. Lett., 1998, 1261.
29 otochemical Electron Transfer C hν >320 nm cat., C 3 C, rt C 3 = (C 2 ) 2 77% = 0% DM * hν DM C C DM DM = (C 2 ) 2 CC 3 hν, (0.2), C 3 C, 12 h (0.2) CC 3 4% 4%
30 CC 3 hν >300 nm (0.2), (0.2) C 3 C (10) CC 3 (C 2 ) 2 C 3 C, 12 h 73% 9% Tetrahedron Lett., 46, 2373 (2005). Ac Ac Ac hν Ac Ac SET BET (Ac) Cl or Cl X - Ac X =, Cl
31 on-otochemical Electron Transfer Catalysts C 3 C 2 C 3 C 2 5 mol%,, C 3 C 2 1,4-dioxane, reflux = C 2 C 2 CC 3 C 3 35% 52% C 3 C 2 xime xime xime xime
32 C % 5 mol% CC 3, C 3 C 2 C 3 C 6 5 1,4-dioxane, reflux C % Chem. Lett., 2002, 144. C 3 C mol% C 3, C 3 C 2 C 6 5 1,4-dioxane, reflux 1 C 3 Bull. Chem. Soc. Jpn., 76, 2003 (2003).
33 Preparation of 3,4-Dihydro-2-pyrroles with Cu(I)-Catalyst C 2 5 mol% CuBr S 2, 3 LiBr II Cu Br (syn : anti = 1 : 1) 1,4-dioxane, 80 C Br II Cu Br Cu I Br 86% CC 6 F 5 CuBr S 2 LiBr 1,4-dioxane, rt, 2 h Br 98% ( 1 : 2.2 ) (C 2 ) 2 cat. 75% ( 1 : 6 ) Li TF 78 or 100 C 2 AllocCl pyridine C 2 Cl 2, 40 C rt Alloc 2 steps 76% peduncularine Bull. Chem. Soc. Jpn., 79, 1552 (2006).
34 1 2 C CC 6 F 5 1) 20 mol% Cu powder 100 mol% (C 2 C 2 2 ) 2 ClC 2 C 2 Cl, 80 C, 1 h Cl Cl 2), C 2 Cl 2, rt, 1 h Cl Cl C CC 6 F 5 adical Cyclization 1 2 Yield / % C t-bu 2 C Bull. Chem. Soc. Jpn., 78, 1659 (2005). S 2 Cl Et 3 S 2 S 2-Type Substituion 95% Chem. Lett., 33, 26 (2004).
35 xime Cl 2-Azirine Cl 2-Azirine 1 2 S 2 C 2 Et 2 mol% [h( 2 CCF 3 ) 2 ] 2 ClC 2 C 2 Cl 60 C, 2 h Vinyl Azide base P. W. eber, et al. Ann., 449, 109 (1926). 90% ClC 2 C 2 Cl, rt, 32 h Chem. Lett., 2007, 36, 52. Et 2 C Cl Cl C quant. C 2 3 c-hexane, 80 C 3 CEt CEt 2 C 2 unstable D. Knittel, Synthesis, 1985, 186. toluene, 100 C, 2 h Et 2 C C 93%
36 Synthesis of Pyrroles from Vinyl Azides toluene 100 o C azirine C 2 Et Et 2 C C C 2 Et 3 cat. Cu[(S 2 CF 3 ) 2 ] 2 Et C 3 C, 2 2 Et Cu II Et 2 C C 2 Et 40 o C Cu complex rg. Lett. 2008, 10, 313.
37 from May, 2007 Catalytic C-C and C- Bond Formation All of the Group mbers Dr. Mitsuru Kitamura (Kyushu Institute of Technology) Dr. Motoki Yamane Dr. Shunsuke Chiba anyang Technological University
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