Nickel catalysis: Synergy between method development and total synthesis

Accounts of Chemical Research

Volumn 48, Issue 5, 2015, Pages 1503-1514

  Standley, Eric A ^a   Tasker, Sarah Z ^a   Jensen, Kim L ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8-HYDROXY-8-METHYL-6-(2'-METHYLHEXYLIDENE)-1-AZABICYCLO(4.3.0)NONANE; AMPHIDINOLIDE T1; AMPHIDINOLIDE T4; BRIDGED BICYCLO COMPOUNDS; GLOEOSPORONE; INDOLIZINE DERIVATIVE; LACTONE; MACROLIDE; NICKEL; ORGANOMETALLIC COMPOUND; TERPESTACIN;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BRIDGED BICYCLO COMPOUNDS; CATALYSIS; INDOLIZINES; LACTONES; MACROLIDES; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84929572712     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00064     Document Type: Article

References (51)

1. Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
2. Montgomery, J. Nickel-Catalyzed Reductive Cyclizations and Couplings Angew. Chem., Int. Ed. 2004, 43, 3890-3908
3. Oblinger, E.; Montgomery, J. A New Stereoselective Method for the Preparation of Allylic Alcohols J. Am. Chem. Soc. 1997, 119, 9065-9066
4. Huang, W.-S.; Chan, J.; Jamison, T. F. Highly Selective Catalytic Intermolecular Reductive Coupling of Alkynes and Aldehydes Org. Lett. 2000, 2, 4221-4223
5. McCarren, P. R.; Liu, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. Mechanism and Transition-State Structures for Nickel-Catalyzed Reductive Alkyne-Aldehyde Coupling Reactions J. Am. Chem. Soc. 2009, 131, 6654-6655
6. Mahandru, G. M.; Liu, G.; Montgomery, J. Ligand-Dependent Scope and Divergent Mechanistic Behavior in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes J. Am. Chem. Soc. 2004, 126, 3698
7. Miller, K. M.; Huang, W.-S.; Jamison, T. F. Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and α-Hydroxy Ketones J. Am. Chem. Soc. 2003, 125, 3442-3443
8. Colby, E. A.; Jamison, T. F. P -Chiral, Monodentate Ferrocenyl Phosphines, Novel Ligands for Asymmetric Catalysis J. Org. Chem. 2003, 68, 156-166
9. Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F. Alkene-Directed, Nickel-Catalyzed Alkyne Coupling Reactions J. Am. Chem. Soc. 2004, 126, 4130-4131
10. Liu, P.; McCarren, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. Origins of Regioselectivity and Alkene-Directing Effects in Nickel-Catalyzed Reductive Couplings of Alkynes and Aldehydes J. Am. Chem. Soc. 2010, 132, 2050-2057
11. Miller, K. M.; Jamison, T. F. Highly Regioselective, Catalytic Asymmetric Reductive Coupling of 1,3-Enynes and Ketones Org. Lett. 2005, 7, 3077-3080
12. Miller, K. M.; Jamison, T. F. Ligand-Switchable Directing Effects of Tethered Alkenes in Nickel-Catalyzed Additions to Alkynes J. Am. Chem. Soc. 2004, 126, 15342-15343
13. Moslin, R. M.; Jamison, T. F. Mechanistic Implications of Nickel-Catalyzed Reductive Coupling of Aldehydes and Chiral 1,6-Enynes Org. Lett. 2006, 8, 455-458
14. Malik, H. A.; Sormunen, G. J.; Montgomery, J. A General Strategy for Regiocontrol in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes J. Am. Chem. Soc. 2010, 132, 6304-6305
15. Jackson, E. P.; Montgomery, J. Regiocontrol in Catalytic Reductive Couplings through Alterations of Silane Rate Dependence J. Am. Chem. Soc. 2015, 137, 958-963
16. Patel, S. J.; Jamison, T. F. Catalytic Three-Component Coupling of Alkynes, Imines, and Organoboron Reagents Angew. Chem., Int. Ed. 2003, 42, 1364-1367
17. Zhou, C.-Y.; Zhu, S.-F.; Wang, L.-X.; Zhou, Q.-L. Enantioselective Nickel-Catalyzed Reductive Coupling of Alkynes and Imines J. Am. Chem. Soc. 2010, 132, 10955-10957
18. Patel, S. J.; Jamison, T. F. Asymmetric Catalytic Coupling of Organoboranes, Alkynes, and Imines with a Removable (Trialkylsilyloxy)ethyl Group-Direct Access to Enantiomerically Pure Primary Allylic Amines Angew. Chem., Int. Ed. 2004, 43, 3941-3944
19. Molinaro, C.; Jamison, T. F. Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides J. Am. Chem. Soc. 2003, 125, 8076-8077
20. Beaver, M. G.; Jamison, T. F. Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes Org. Lett. 2011, 13, 4140-4143
21. Chan, J.; Jamison, T. F. Synthesis of (-)-Terpestacin via Catalytic, Stereoselective Fragment Coupling: Siccanol Is Terpestacin, Not 11- epi -Terpestacin J. Am. Chem. Soc. 2003, 125, 11514-11515
22. Colby, E. A.; OBrien, K. C.; Jamison, T. F. Synthesis of Amphidinolide T1 via Catalytic, Stereoselective Macrocyclization J. Am. Chem. Soc. 2004, 126, 998-999
23. Colby, E. A.; OBrien, K. C.; Jamison, T. F. Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations J. Am. Chem. Soc. 2005, 127, 4297-4307
24. Moslin, R. M.; Jamison, T. F. Total Synthesis of (+)-Acutiphycin J. Org. Chem. 2007, 72, 9736-9745
25. Trenkle, J. D.; Jamison, T. F. Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (-)-Gloeosporone Angew. Chem., Int. Ed. 2009, 48, 5366-5368
26. Woodin, K. S.; Jamison, T. F. Total Synthesis of Pumiliotoxins 209F and 251D via Late-Stage, Nickel-Catalyzed Epoxide-Alkyne Reductive Cyclization J. Org. Chem. 2007, 72, 7451-7454
27. Ng, S.-S.; Jamison, T. F. Highly Enantioselective and Regioselective Nickel-Catalyzed Coupling of Allenes, Aldehydes, and Silanes J. Am. Chem. Soc. 2005, 127, 7320-7321
28. Ng, S.-S.; Jamison, T. F. Enantioselective and Regioselective Nickel-Catalyzed Multicomponent Coupling of Chiral Allenes, Aromatic Aldehydes, and Silanes Tetrahedron 2005, 61, 11405-11417
29. Ng, S.-S.; Jamison, T. F. Nickel-Catalyzed Coupling of Terminal Allenes, Aldehydes, and Silanes Tetrahedron 2006, 62, 11350-11359
30. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. Interactions of Aziridines with Nickel Complexes: Oxidative-Addition and Reductive-Elimination Reactions That Break and Make C-N Bonds J. Am. Chem. Soc. 2002, 124, 2890-2891
31. Huang, C.-Y.; Doyle, A. G. Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines J. Am. Chem. Soc. 2012, 134, 9541-9544
32. Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G. Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines J. Am. Chem. Soc. 2013, 135, 13605-13609
33. Jensen, K. L.; Standley, E. A.; Jamison, T. F. Highly Regioselective Nickel-Catalyzed Cross-Coupling of N -Tosylaziridines and Alkylzinc Reagents J. Am. Chem. Soc. 2014, 136, 11145-11152
34. Ng, S.-S.; Jamison, T. F. Simple Alkenes as Substitutes for Organometallic Reagents: Nickel-Catalyzed, Intermolecular Coupling of Aldehydes, Silyl Triflates, and Alpha Olefins J. Am. Chem. Soc. 2005, 127, 14194-14195
35. Ho, C.-Y.; Ng, S.-S.; Jamison, T. F. Nickel-Catalyzed, Carbonyl-Ene-Type Reactions: Selective for α-Olefins and More Efficient with Electron-Rich Aldehydes J. Am. Chem. Soc. 2006, 128, 5362-5363
36. Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Nickel-Catalyzed Homoallylation of Aldehydes and Ketones with 1,3-Dienes and Complementary Promotion by Diethylzinc or Triethylborane Angew. Chem., Int. Ed. 1999, 38, 397-400
37. Ogoshi, S.; Oka, M.-a.; Kurosawa, H. Direct Observation of Oxidative Cyclization of η2-Alkene and η2-Aldehyde on Ni(0) Center. Significant Acceleration by Addition of Me3SiOTf J. Am. Chem. Soc. 2004, 126, 11802-11803
38. Ho, C.-Y.; Schleicher, K. D.; Chan, C.-W.; Jamison, T. F. Catalytic Addition of Simple Alkenes to Carbonyl Compounds by Use of Group 10 Metals Synlett 2009, 2565-2582
39. Ng, S.-S.; Ho, C.-Y.; Jamison, T. F. Nickel-Catalyzed Coupling of Alkenes, Aldehydes, and Silyl Triflates J. Am. Chem. Soc. 2006, 128, 11513-11528
40. Ho, C.-Y.; Jamison, T. F. Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by [Ni(NHC){P(OPh)3}]: Synergy Between a Strong σ-Donor and a Strong π-Acceptor Angew. Chem., Int. Ed. 2007, 46, 782-785
41. Yamamoto, T.; Yamamoto, A.; Ikeda, S. Study of Organo(dipyridyl)nickel Complexes. I. Stability and Activation of the Alkyl-Nickel Bonds of Dialkyl(dipyridyl)nickel by Coordination with Various Substituted Olefins J. Am. Chem. Soc. 1971, 93, 3350-3359
42. Ho, C.-Y.; Ohmiya, H.; Jamison, T. F. α-Olefins as Alkenylmetal Equivalents in Catalytic Conjugate Addition Reactions Angew. Chem., Int. Ed. 2008, 47, 1893-1895
43. Matsubara, R.; Jamison, T. F. Nickel-Catalyzed Allylic Substitution of Simple Alkenes J. Am. Chem. Soc. 2010, 132, 6880-6881
44. Matsubara, R.; Gutierrez, A. C.; Jamison, T. F. Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins J. Am. Chem. Soc. 2011, 133, 19020-19023
45. Standley, E. A.; Jamison, T. F. Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes J. Am. Chem. Soc. 2013, 135, 1585-1592
46. Standley, E. A.; Smith, S. J.; Müller, P.; Jamison, T. F. A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes Organometallics 2014, 33, 2012-2018
47. Qin, L.; Ren, X.; Lu, Y.; Li, Y.; Zhou, J. Intermolecular Mizoroki-Heck Reaction of Aliphatic Olefins with High Selectivity for Substitution at the Internal Position Angew. Chem., Int. Ed. 2012, 51, 5915-5919
48. Qin, L.; Hirao, H.; Zhou, J. Regioselective Heck Reaction of Aliphatic Olefins and Aryl Halides Chem. Commun. 2013, 49, 10236-10238
49. Zou, Y.; Qin, L.; Ren, X.; Lu, Y.; Li, Y.; Zhou, J. Selective Arylation and Vinylation at the α Position of Vinylarenes Chem.-Eur. J. 2013, 19, 3504-3511
50. Tasker, S. Z.; Gutierrez, A. C.; Jamison, T. F. Nickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Products Angew. Chem., Int. Ed. 2014, 53, 1858-1861
51. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Recent Advances in Homogeneous Nickel Catalysis Nature 2014, 509, 299-309