Methods and Mechanisms for Cross-Electrophile Coupling of Csp2 Halides with Alkyl Electrophiles

Accounts of Chemical Research

Volumn 48, Issue 6, 2015, Pages 1767-1775

  Weix, Daniel J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZYL DERIVATIVE; HALOGENATED HYDROCARBON; KETONE; NICKEL;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; BENZYL COMPOUNDS; CATALYSIS; HYDROCARBONS, HALOGENATED; KETONES; MOLECULAR STRUCTURE; NICKEL;

EID: 84934896311     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00057     Document Type: Article

References (61)

1. Everson, D. A.; Weix, D. J. Cross-Electrophile Coupling: Principles of Reactivity and Selectivity J. Org. Chem. 2014, 79, 4793-4798
2. Knappke, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Reductive Cross-Coupling Reactions between Two Electrophiles Chem.-Eur. J. 2014, 20, 6828-6842
3. Moragas, T.; Correa, A.; Martin, R. Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds Chem.-Eur. J. 2014, 20, 8242-8258
4. Wurtz, A. Ueber eine neue Klasse organischer Radicale Ann. Chem. Pharm. 1855, 96, 364-375
5. Ullmann, F.; Bielecki, J. Ueber Synthesen in der Biphenylreihe Chem. Ber. 1901, 34, 2174-2185
6. Chaussard, J.; Folest, J.-C.; Nedelec, J.-Y.; Perichon, J.; Sibille, S.; Troupel, M. Use of Sacrificial Anodes in Electrochemical Functionalization of Organic Halides Synthesis 1990, 369-381
7. Nédélec, J.-Y.; Périchon, J.; Troupel, M. Organic electroreductive coupling reactions using transition metal complexes as catalysts: Electrochemistry VI Electroorganic Synthesis: Bond Formation at Anode and Cathode Top. Curr. Chem. 1997, 185, 141-173
8. Jutand, A. Contribution of Electrochemistry to Organometallic Catalysis Chem. Rev. 2008, 108, 2300-2347
9. Klein, A.; Budnikova, Y.; Sinyashin, O. Electron transfer in organonickel complexes of α-diimines: Versatile redox catalysts for C-C or C-P coupling reactions-A review J. Organomet. Chem. 2007, 692, 3156-3166
10. Frisch, A. C.; Beller, M. Catalysts for Cross-Coupling Reactions with Non-activated Alkyl Halides Angew. Chem., Int. Ed. 2005, 44, 674-688
11. Rudolph, A.; Lautens, M. Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions Angew. Chem., Int. Ed. 2009, 48, 2656-2670
12. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2009.
13. 2-Br Bond Activation in Palladium-Catalysed Suzuki Cross-Coupling: An Experimental and Theoretical Study of the Role of Phosphine Ligands Chem.-Eur. J. 2010, 16, 13390-13397
14. Ariafard, A.; Lin, Z. Understanding the Relative Easiness of Oxidative Addition of Aryl and Alkyl Halides to Palladium(0) Organometallics 2006, 25, 4030-4033
15. Gonzalez-Bobes, F.; Fu, G. Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids J. Am. Chem. Soc. 2006, 128, 5360-5361
16. Jones, G. D.; McFarland, C.; Anderson, T. J.; Vicic, D. A. Analysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions Chem. Commun. 2005, 4211-4213
17. Everson, D. A.; Weix, D. J. Unpublished results from thesis work.
18. Everson, D. A.; Shrestha, R.; Weix, D. J. Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides J. Am. Chem. Soc. 2010, 132, 920-921
19. Takahashi, H.; Inagaki, S.; Nishihara, Y.; Shibata, T.; Takagi, K. Novel Rh Catalysis in Cross-Coupling between Alkyl Halides and Arylzinc Compounds Possessing ortho-COX (X = OR, NMe2, or Ph) Groups Org. Lett. 2006, 8, 3037-3040
20. Prinsell, M. R.; Everson, D. A.; Weix, D. J. Nickel-Catalyzed, Sodium Iodide-Promoted Reductive Dimerization of Alkyl Halides, Alkyl Pseudohalides, and Allylic Acetates Chem. Commun. 2010, 46, 5743-5745
21. Everson, D. A.; Jones, B. A.; Weix, D. J. Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides J. Am. Chem. Soc. 2012, 134, 6146-6159
22. McCann, L. C.; Organ, M. G. On The Remarkably Different Role of Salt in the Cross-Coupling of Arylzincs From That Seen With Alkylzincs Angew. Chem., Int. Ed. 2014, 53, 4386-4389
23. Sase, S.; Jaric, M.; Metzger, A.; Malakhov, V.; Knochel, P. One-Pot Negishi Cross-Coupling Reactions of In Situ Generated Zinc Reagents with Aryl Chlorides, Bromides, and Triflates J. Org. Chem. 2008, 73, 7380-7382
24. Everson, D. A.; George, D. T.; Weix, D. J.; Buergler, J. F.; Wood, J. L. Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate Org. Synth. 2013, 90, 200-214
25. dIncan, E.; Sibille, S.; Perichon, J.; Moingeon, M.-O.; Chaussard, J. Electrosynthesis of ketones from organic halides and anhydrides Tetrahedron Lett. 1986, 27, 4175-4176
26. Marzouk, H.; Rollin, Y.; Folest, J. C.; Nédélec, J. Y.; Périchon, J. Electrochemical synthesis of ketones from acid chlorides and alkyl and aryl halides catalysed by nickel complexes J. Organomet. Chem. 1989, 369, C47-C50
27. Amatore, C.; Jutand, A.; Périchon, J.; Rollin, Y. Mechanism of the Nickel-Catalyzed Electrosynthesis of Ketones by Heterocoupling of Acyl and Benzyl Halides Monatsh. Chem. 2000, 131, 1293-1304
28. Onaka, M.; Matsuoka, Y.; Mukaiyama, T. A Convenient Method for the Direct Preparation of Ketones from 2-(6-(2-Methoxyethyl)Pyridyl)Carboxylates and Alkyl Iodides by Use of Zinc Dust and a Catalytic Amount of Nickel Dichloride Chem. Lett. 1981, 10, 531-534
29. Wotal, A. C.; Weix, D. J. Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides Org. Lett. 2012, 14, 1476-1479
30. 3CN as an excellent condensing system for.beta.-lactam formation from.beta.-amino acids J. Am. Chem. Soc. 1981, 103, 2406-2408
31. Wang, S.; Qian, Q.; Gong, H. Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate Org. Lett. 2012, 14, 3352-3355
32. Everson, D. A.; Buonomo, J. A.; Weix, D. J. Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides Synlett 2014, 25, 233-238
33. Hegedus, L. S.; Miller, L. L. Reaction of π-allylnickel bromide complexes with organic halides. Stereochemistry and mechanism J. Am. Chem. Soc. 1975, 97, 459-460
34. Durandetti, M.; Nédélec, J.-Y.; Périchon, J. Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides J. Org. Chem. 1996, 61, 1748-1755
35. Biswas, S.; Weix, D. J. Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides J. Am. Chem. Soc. 2013, 135, 16192-16197
36. Wotal, A. C.; Ribson, R. D.; Weix, D. J. Stoichiometric Reactions of Acylnickel(II) Complexes with Electrophiles and the Catalytic Synthesis of Ketones Organometallics 2014, 33, 5874-5881
37. Zhao, C.; Jia, X.; Wang, X.; Gong, H. Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides J. Am. Chem. Soc. 2014, 136, 17645-17651
38. Yin, H.; Zhao, C.; You, H.; Lin, K.; Gong, H. Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides Chem. Commun. 2012, 48, 7034-7036
39. 5-cyclopentadienyl)tricarbonylhydridovanadate. A comparative mechanistic study of its organic halide reduction reactions with those of tri- n -butyltin hydride J. Am. Chem. Soc. 1978, 100, 7902-7915
40. Fischer, H. The Persistent Radical Effect: A Principle for Selective Radical Reactions and Living Radical Polymerizations Chem. Rev. 2001, 101, 3581-3610
41. Studer, A. The Persistent Radical Effect in Organic Synthesis Chem.-Eur. J. 2001, 7, 1159-1164
42. Amatore, M.; Gosmini, C. Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides Chem.-Eur. J. 2010, 16, 5848-5852
43. RajanBabu, T. V.; Nugent, W. A. Selective Generation of Free Radicals from Epoxides Using a Transition-Metal Radical. A Powerful New Tool for Organic Synthesis J. Am. Chem. Soc. 1994, 116, 986-997
44. Gansäuer, A.; Pierobon, M.; Bluhm, H. Catalytic, Highly Regio- and Chemoselective Generation of Radicals from Epoxides: Titanocene Dichloride as an Electron Transfer Catalyst in Transition Metal Catalyzed Radical Reactions Angew. Chem., Int. Ed. 1998, 37, 101-103
45. Gansäuer, A.; Lauterbach, T.; Bluhm, H.; Noltemeyer, M. A Catalytic Enantioselective Electron Transfer Reaction: Titanocene-Catalyzed Enantioselective Formation of Radicals from meso-Epoxides Angew. Chem., Int. Ed. 1999, 38, 2909-2910
46. Zhao, Y.; Weix, D. J. Nickel-Catalyzed Regiodivergent Opening of Epoxides with Aryl Halides: Co-Catalysis Controls Regioselectivity J. Am. Chem. Soc. 2014, 136, 48-51
47. Zhao, Y.; Weix, D. J. Enantioselective Cross-Coupling of meso-Epoxides with Aryl Halides J. Am. Chem. Soc. 2015, 137, 3237-3240
48. Hipler, B.; Uhlig, E. Benzylnickel(II)-Komplexe und ihre Reaktionen Z. Anorg. Allg. Chem. 1984, 510, 11-15
49. Ackerman, L. K. G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides Chem. Sci. 2015, 6, 1115-1119
50. Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. Preparation of alkylchromium reagents by reduction of alkyl halides with chromium(II) chloride under cobalt catalysis J. Org. Chem. 1989, 54, 4732-4734
51. Molander, G. A.; Traister, K. M.; ONeill, B. T. Reductive Cross-Coupling of Nonaromatic, Heterocyclic Bromides with Aryl and Heteroaryl Bromides J. Org. Chem. 2014, 79, 5771-5780
52. Molander, G. A.; Wisniewski, S. R.; Traister, K. M. Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides Org. Lett. 2014, 16, 3692-3695
53. Singh, R.; Bordeaux, M.; Fasan, R. P450-Catalyzed Intramolecular sp3 C-H Amination with Arylsulfonyl Azide Substrates ACS Catal. 2014, 4, 546-552
54. Morofuji, T.; Shimizu, A.; Yoshida, J.-i. Direct C-N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C-H Functionalization J. Am. Chem. Soc. 2014, 136, 4496-4499
55. Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones J. Am. Chem. Soc. 2013, 135, 7442-7445
56. Cherney, A. H.; Reisman, S. E. Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones Tetrahedron 2014, 70, 3259-3265
57. Choi, J.; Martín-Gago, P.; Fu, G. C. Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones J. Am. Chem. Soc. 2014, 136, 12161-12165
58. Schley, N. D.; Fu, G. C. Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation J. Am. Chem. Soc. 2014, 136, 16588-16593
59. Tellis, J. C.; Primer, D. N.; Molander, G. A. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis Science 2014, 345, 433-436
60. Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.; MacMillan, D. W. C. Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides Science 2014, 345, 437-440
61. For an early example of the combination of palladium catalysis with photoredox-generated radicals, see: Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S.; Room-Temperature, C-H Arylation: Merger of Pd-Catalyzed C-H Functionalization and Visible-Light Photocatalysis J. Am. Chem. Soc. 2011, 133, 18566-18569