Couplings: Recent Developments in Cross-Couplings: Acids with Carbonyls. and Boronic. Wen Yuan
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1 Recent Developments in Cross-Couplings: Couplings: Coupling Boronates with Inert C- C Bonds, and Boronic Acids with Carbonyls Wen Yuan
![Cross-Coupling Reaction The reaction of organometallic reagents with organic electrophiles in the presence of metal catalysts [M]: Group 8 10 Metal catalysts Fe, Co, i, Cu, Pd, Ru, Rh X: I, Br, Cl,](/docs-images/76/74032844/images/2-0.jpg "Tf C-C, C-, C-, C-S, C-P, etc. m: Mg, B, Si, Sn, Zn, Al Study of Transition Metal Catalyst Total Synthesis of atural Product Synthesis of Macromolecule Miyaura,.")
2 Cross-Coupling Reaction The reaction of organometallic reagents with organic electrophiles in the presence of metal catalysts [M]: Group 8 10 Metal catalysts Fe, Co, i, Cu, Pd, Ru, Rh X: I, Br, Cl, Tf C-C, C-, C-, C-S, C-P, etc. m: Mg, B, Si, Sn, Zn, Al Study of Transition Metal Catalyst Total Synthesis of atural Product Synthesis of Macromolecule Miyaura,. Cross-Coupling Reactions: A Practical Guide. Springer:
3 Importance in Total Synthesis of Haplophytine H Me Me H Me Me Haplophytine Suzuki-Miyaura coupling Pd(dppf)Cl 2 TlEt Bn Me Cbz + BPin Me C 2 Me TBS I C 2 TMSE Haplophyton Cimicidum Isolated by Snyder, 1952 Total synthesis by icolaou, 2009 icolaou, K. C.; Dalby, S. M.; i, S.; Suzuki, T.; Chen, D. Y. Angew. Chem. Int. Ed. 2009, 48,
4 Suzuki-Miyaura Coupling Matos, K.; Soderquist, J. A. J. rg. Chem. 1998, 63, 461 Miyaura,. Cross-Coupling Reactions: A Practical Guide. Springer:
5 Why on-halogen Coupling Cost R-I Commercial availability Facile preparation Environment friendly rganic Electrophile R-Tf R-Br R-Ac R-H R: Price $/mol 5
6 Suzuki-Miyaura Coupling 2 R-R' [Pd] R-X R Pd R' 3 B(H) 3 + X - path A R' H B H H 2 R X=I, Br, Cl, Tf path C Pd X 1 R'' - (H) 2 B R'' 5 R' Pd R R'-B(H) 2 path B Matos, K.; Soderquist, J. A. J. rg. Chem. 1998, 63, 461 Miyaura,. Cross-Coupling Reactions: A Practical Guide. Springer: 2002 R Pd R'' 4 R-R'' 6
7 General utline Aromatic Ether Tautomerizable Heterocycle Aromatic Ester From Ketone to Tosylhydrazones 7
8 General utline Aromatic Ether Tautomerizable Heterocycle R 1 C R 2 Aromatic Ester From Ketone to Tosylhydrazones 8
9 xidative Addition R-X [M] R M X PPh 2 CH 3 RhCl(PPh 3 ) 3 PPh 2 Ph 2 P CH 3 RhCl P Ph 2 Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255. van der Boom, M. E.; iou, S.-Y.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1998, 120,
10 Ru Catalyst for Suzuki Coupling PPh 3 H H Ru PPh 3 PPh 3 C How does Ru activate C- bond? What is the selectivity between the C-H and C- bond? What is the reasonable mechanism? What is the deficiency in this chemistry and how to improve it? Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2004, 126,
11 Chelating Assistance for C- Activation run ketone product yield Me Ph 1 96% 2 Me Me Ph Ph 0%? Ph 3 P C Ru R Me Ph 3 75% PPh 3 Me Me Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2004, 126,
12 Crystal Structure of Intermediate RuH 2 (C)(PPh 3 ) 3 + Ar toluene reflux, 20h Ar=p-C 6 H 4 CH 3 Ph 3 P C Ru Ar PPh 3 By Discovery Studio ViewerPro Ueno, S.; Mizushima, E.; Chatani,.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128,
13 Proposed Mechanism Mechanism : Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2004, 126,
14 Selectivity of Activation C-H activation C- activation Kakiuchi, F.; Kan, S.; Igi, K.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2003, 125, Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2004, 126,
15 C- Activation vs C-H Activation H H Ph RuH 2 (C)(PPh 3 ) 3 + Ph B VS toluene, reflux Me Ph Me Bond Dissociation Energy 15
16 C- Activation vs C-H Activation Bond Dissociation Energy 1 HMR 31 PMR FAB-MS Intermediate bserved by MR A ; (M + -H) B o Ru-H (M + -H) Ueno, S.; Mizushima, E.; Chatani,.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128,
17 C- Activation vs C-H Activation Bond Dissociation Energy 1 HMR 31 PMR FAB-MS Intermediate bserved by MR A ; (M + -H) B o Ru-H (M + -H) Thermodynamic product Ueno, S.; Mizushima, E.; Chatani,.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, Kinetic product 17
18 Scope of rganoboronates Me + Ph B RuH 2 (C)(PPh 3 ) 3 toluene, reflux Ph CH 3 CF 3 Me 2 86% 89% 84% 83% 81% Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani,.; Murai, S. J. Am. Chem. Soc. 2004, 126,
19 Deficiency and Improvement 1. rtho Position 2. Price Pd 334 Metal Ru 80 i 0.55 Updated ct $/oz R=Me 93% Tobisu, M.; Shimasaki, T.; Chatani,. Angew. Chem. Int. Ed. 2008, 47,
20 Application on Synthesis of ligoarenes Symmetric oligoarenes ittke, A. F.; Dai, C. Y.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, i, H. Personal communication Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, Asymmetric oligoarenes
21 Application on Synthesis of ligoarenes B(H) 2 Me cat. [Pd(PPh 3 ) 4 ] a 2 C 3 Me Br 50g/225$ toluene/h 2 reflux, 12h 77% B cat. [i(cod) 2 ]/PCy 3 toluene, CsF 120 o C, 12h 95% 21 Tobisu, M.; Shimasaki, T.; Chatani,. Angew. Chem. Int. Ed. 2008, 47, 4866.
22 General utline Aromatic Ether Tautomerizable Heterocycle R 1 C R 2 Aromatic Ester From Ketone to Tosylhydrazones 22
23 Starting from Trost-Tsuji Reaction Allyl C- bond is weaker than Acyl C- bond Ac [Pd] Pd Ac Pd (II) Ac - allyl Pd (II) Pd (II) u reductive elimination u u - -Pd 2 uo, Y.-R.; Holmes, J.. J. Phys. Chem. 1994, 98, 303. Trost, B. M.; VanVranken, D.. Chem. Rev. 1996, 96, 395.
24 Allyl Acetate vs Aryl Acetate Allyl C- bond is weaker than Acyl C- bond uo, Y.-R.; Holmes, J.. J. Phys. Chem. 1994, 98, 303. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36,
25 Acyl C- Bond Cleavage -C C Me decarbonylation i Ph + Me i Ph +C disproportionation (A) - i 2 RCPh oxidative addition CR i Ph =PPh 3 -C decarbonylation 2 i Ph H -C 2 H 4 elimination H 2 i Ph + +C reductive elimination (B) Yamamoto, T.; Ishizu, J.; Kohara, T.; Komiya, S.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102,
26 Aryl C- Bond Cleavage Quasdorf, K. W.; Tian, X.; Garg,. K. J. Am. Chem. Soc. 2008, 130, Guan, B. T.; Wang, Y.; i, B. J.; Yu, D. G.; Shi, Z. J. J. Am. Chem. Soc. 2008, 130,
27 Proposed Mechanism for Shi s work Guan, B. T.; Wang, Y.; i, B. J.; Yu, D. G.; Shi, Z. J. J. Am. Chem. Soc. 2008, 130,
28 Two Pathways for xidative Addition i Ac i TS1 Ac i Ac Ac i PhAc I2 I3 I4 i I1 + - =PPh 3 I: Intermediate TS: Transition State i PhAc bis-phosphine mechanism i Ac i TS2 Ac i C I5 I6 I7 mono-phosphine mechanism i, Z.; Zhang, S..; Fu, Y.; Guo, Q. X.; iu,. J. Am. Chem. Soc. 2009, 131,
29 Energy Comparison between Two Pathways i Ac TS i I1 0.0 I2 I I TS2 Unit: kcal/mol xidative Addition of PhAc to i(0) prefer the monophosphine mechanism i, Z.; Zhang, S..; Fu, Y.; Guo, Q. X.; iu,. J. Am. Chem. Soc. 2009, 131, 8815 i I3 Ac 17.9 I4 I7 Ac i 5.3 i C
30 Transmetallation & Elimination Base-assisted Transmetallation: i C I7 H K[PhB(H) 3 ] H H B i K H I10 KAc H i B(H)2 I11 i B(H)2 TS4 H i I12 B(H) 2 B(H) 3 i I13 Energy Barrier = 31.2 kcal/mol i, Z.; Zhang, S..; Fu, Y.; Guo, Q. X.; iu,. J. Am. Chem. Soc. 2009, 131,
31 Transmetallation & Elimination Base-assisted Transmetallation: i C I7 H K[PhB(H) 3 ] H H B i K H I10 KAc H i B(H)2 I11 i B(H)2 TS4 H i I12 B(H) 2 B(H) 3 i I13 Energy Barrier = 31.2 kcal/mol Reductive Elimination: i i I13 i, Z.; Zhang, S..; Fu, Y.; Guo, Q. X.; iu,. J. Am. Chem. Soc. 2009, 131, 8815 TS5 i I5 + - i I1 Energy Barrier = 6.0 kcal/mol 31
32 Two more Questions Discussed Why stronger Aryl C- bond? Why i not Pd in this chemistry? Unit: kcal/mol M M=i, Pd PhX M complex X TS M X M X Ph-X i(0) barrier Pd(0) barrier Ph-Br Ph-Ac Ph-HAc High reverse barrier is the major reason! i, Z.; Zhang, S..; Fu, Y.; Guo, Q. X.; iu,. J. Am. Chem. Soc. 2009, 131, 8815 Energy Barrier from η 2 complex to TS is the major reason! 32
33 ne-pot Reaction H H H Me H 1. PivCl, Et 3, CH 2 Cl 2 2. (4-MePhB) 3,i(PCy 3 ) 2 Cl 2 K 3 P 4,H 2, Dioxane H H Me H Estrone 62% yield Quasdorf, K. W.; Tian, X.; Garg,. K. J. Am. Chem. Soc. 2008, 130,
34 atest Examples of Ester Coupling Piv + PhZnCl icl 2 (PCy 3 ) 2 (5 mol%) THF/DMA 70 o C 84% yield Ph i, B. J.; i, Y. Z.; u, X. Y.; iu, J.; Guan, B. T.; Shi, Z. J. Angew. Chem. Int. Ed. 2008, 47, i, B. J.; Xu,.; Wu, Z. H.; Guan, B. T.; Sun, C..; Wang, B. Q.; Shi, Z. J. J. Am. Chem. Soc. 2009, 131, Yu, J. Y.; Kuwano, R. Angew. Chem. Int. Ed. 2009, 48, 7217.
35 Conclusion for Part 1 and 2 Chelation assistance helps Ru catalyst to activate inert C- bond in aromatic ethers Cheaper i catalyst can activate aryl C- bond in ether or ester for Suzuki coupling Computation studies help propose and understand the mechanism 35
36 General utline Aromatic Ether Tautomerizable Heterocycle Aromatic Ester From Ketone to Tosylhydrazones 36
37 Tautomerizable Heterocycles H H H H H Vitamin B2 37
38 Synthetic Route for 6-arylpurine ucleosides H Ar H traditional multi-step transformation H H H X H H <40% protection P deprotection P P Ar P H activation functionalization P P P P P Kang, F. A.; Sui, Z. H.; Murray, W. V. J. Am. Chem. Soc. 2008, 130,
39 Activation of Carbonyl Group Cl H PCl 3 /Ph(Me) 2 MeC/ TMSBr Butanone -40 o C ai Butanone -40 o C Br I preformation Reactivity order in transition metal catalyzed couplings: C-I>C-Br,C-Tf,C-P + >C-Cl iu, J.; Robins, M. J. J. Am. Chem. Soc. 2007, 129,
40 ne-step Conversion Kang, F. A.; Sui, Z. H.; Murray, W. V. J. Am. Chem. Soc. 2008, 130,
41 Castro s Reagent Han, S. Y.; Kim, Y. A. Tetrahedron 2004, 60, Kang, F. A.; Sui, Z. H.; Murray, W. V. J. Am. Chem. Soc. 2008, 130,
42 Scope of Phosphonium Salts Environmental Consideration & Reactivity PyBP P + PF 6 Side reaction & atom economic Heterocycle Coste, J.; Dufour, M..; Pantaloni, A.; Castro, B. Tetrahedron ett. 1990, 31, 669. Delarue, S.; Sergheraert, C. Tetrahedron ett. 1999, 40,
43 Proposed Catalytic Cycle Kang, F. A.; Sui, Z. H.; Murray, W. V. J. Am. Chem. Soc. 2008, 130,
44 Intermediates Verified by MR hypoxanthine Wan, Z. K.; Wacharasindhu, S.; evins, C. G.; in, M.; Tabei, K.; Mansour, T. S. J. rg. Chem. 2007, 72, P MR spectrum 44
45 Single Step Transformation of C 6 -modified ucleosides H H H CH 2 H PyBroP,ArB(H) 2, PdCl 2 (PPh 3 ) 2, 70-72% H H H PyBroP, ArH 80-84% H H H H H H PyBroP ArSH,82-88% S H H PyBroP ArH 2,70-75% H H H H H H 45 Kang, F. A.; Sui, Z. H.; Murray, W. V. Eur. J. rg. Chem. 2009, 461.
46 General utline Aromatic Ether Tautomerizable Heterocycle Aromatic Ester From Ketone to Tosylhydrazones 46
![Diazo Compound in Pd Coupling Reaction Ph HTs + Br [Pd], igand Base, Solvent 70 o C, 4h Ph 98% Roglans, A.](/docs-images/76/74032844/images/47-1.jpg "; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622 Barluenga, J.; Moriel, P.; Valdes, C.; Aznar, F. Angew. Chem. Int. Ed.")
47 Diazo Compound in Pd Coupling Reaction Ph HTs + Br [Pd], igand Base, Solvent 70 o C, 4h Ph 98% Roglans, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622 Barluenga, J.; Moriel, P.; Valdes, C.; Aznar, F. Angew. Chem. Int. Ed. 2007, 46,
48 Bamford-Stevens Reaction Base R 2 R 1 2 S CH 3 R 2 R 1 Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952,
49 Metal Free Coupling by Tosylhydrazones HTs + B(H) 2 Me K 2 C 3 Dioxane 110 o C H Me Metal free reaction 93% ne-pot reaction Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. ature Chemistry 2009, 1,
50 Proposed Mechanism Mechanism HTs Ts -Ts - R 1 R 2 B - R 1 R 2 R 1 R Ar-B(H) 2 R 2 R 1 B H H Ar 4 R 1 R 1 R 2 B(H) Ar 2 R H Ar R 1 R 2 Ar-B(H) 2 5 R 2 R 1 Ar 6 B H H Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. ature Chemistry 2009, 1,
51 Mechanism Studies Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. ature Chemistry 2009, 1,
52 Scope of Tosylhydrazones and Boronic Acids Hydrazone Boronic acid Product R 3 -B(H) 2 K 2 C 3 HTs R 1 R 2 R 2 R 1 Dioxane 110 o C H R 3 Ph Ar 1 HTs B(H) 2 Me H 95% Me HTs B(H) 2 H Br Br 98% B(H) 2 Br HTs H Br Ph 99% HTs (CH CH 3 (CH 2 ) 5 B(H) 2 ) 5 CH 3 2 H 69% HTs Ar 2 B(H) 2 Ar 1 Ar 2 Ar 1 Ar 2 1:2 HTs Ar B(H) 2 Ar Ar Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. ature Chemistry 2009, 1, :1
53 [1,3]-borotropic Rearrangement Ar 1 HTs + K 2 C 3 Ar 2 B(H) 2 Ar 1 Ar 2 + Ar 1 Ar 2 Dioxane 110 o C 1 : 2 H B H Ar 2 H B H Ar2 Ar 1 Ar 1 K 2 C 3 HTs + Ar B(H) 2 Ar + Ar Dioxane 110 o C 1 : 1 Ar B(H) 2 (H) 2 B Ar Henriksen, U.; Snyder, J. P.; Halgren, T. A. J. rg. Chem. 1981, 46, Fang, G. Y.; Aggarwal, V. K. Angew. Chem. Int. Ed. 2007, 46,
54 Conclusion Ru and i can activate the inert C bond in ether or ester group for Suzuki Coupling. Castro s Reagent was used for C C bond formation and application for one step modification of nucleosides. Metal-free reductive coupling directly via Carbonyl group under Suzuki condition 54
55 Acknowledgement Dr. Baker Dr. Borhan Dr. Smith, Dr. Maleczka, Dr. Jackson Dr. iu, Dr. Shi Baker s Group: Hui, Gina, Heyi, Quanxuan, Yiding. Hong, i, Yong, Hao. All of you 55
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