RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2012; 23(8): 1103-1107
DOI: 10.1055/s-0031-1290765
DOI: 10.1055/s-0031-1290765
synpacts
The Use of Tertiary Alkylmagnesium Nucleophiles in Ni-Catalyzed Cross-Coupling Reactions
Authors
Weitere Informationen
Publikationsverlauf
Received: 23. Januar 2012
Accepted: 08. Februar 2012
Publikationsdatum:
20. April 2012 (online)
Abstract
Nickel-catalyzed cross-coupling reactions of unactivated tertiary alkyl nucleophiles and aryl bromides have been developed using N-heterocyclic carbene ligands. These processes are reviewed alongside earlier attempts to employ unactivated tertiary alkyl nucleophiles in cross-coupling reactions. Potential mechanisms for the transformations, and future challenges in this field are discussed.
-
References and Notes
- 1 Metal-Catalyzed Cross-Coupling Reactions . de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
- 2a Chemler SR, Trauner D, Danishefsky SJ. Angew. Chem. Int. Ed. 2001; 40: 4544
Reference Ris Wihthout Link
- 2b Netherton MR, Fu GC In Topics in Organometallic Chemistry: Palladium in Organic Synthesis . Tsuji J. Springer; New York: 2005: 85-108
- 2c Rudolph A, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 2656
- 2d Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417 ; and references cited therein
Reference Ris Wihthout Link
-
For examples of secondary nucleophiles in Pd catalysis, see:
- 3a Campos KR, Klapars A, Walsman JH, Dormer PG, Chen C. J. Am. Chem. Soc. 2006; 128: 3538
- 3b Dreher SD, Dormer PG, Sandrock DL, Molander GA. J. Am. Chem. Soc. 2008; 130: 9257
- 3c Han C, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 7532
- 3d Thaler T, Haag B, Gavryushin A, Schober K, Hartman E, Gschwing RM, Zipse H, Mayer P, Knochel P. Nat. Chem. 2010; 2: 125
- 3e Nakao Y, Takeda M, Matsumoto T, Hiyama T. Angew. Chem. Int. Ed. 2010; 45: 4447
- 3f Sandrock DL, Jean-Gerard L, Chen C.-Y, Dreher SD, Molander GA. J. Am. Chem. Soc. 2010; 132: 17108
- 3g Thaler T, Guo L.-N, Mayer P, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 2147
- 3h Calimsiz S, Organ MG. Chem. Commun. 2011; 47: 5181
- 3i For recent examples of secondary nucleophiles in Ni catalysis, see: Melzig L, Gavryushin A, Knochel P. Org. Lett. 2007; 9: 5529
- 3j See also: Smith SW, Fu GC. Angew. Chem. Int. Ed. 2008; 47: 9334
- 3k See also: Phapale VB, Guisan-Ceinos M, Bunuel E, Cardenas DJ. Chem. Eur. J. 2009; 15: 12681
- 3l See also: Joshi-Pangu A, Ganesh M, Biscoe MR. Org. Lett. 2011; 13: 1218
- 4 Hintermann L, Xiao L, Labonne A. Angew. Chem. Int. Ed. 2008; 47: 8246
- 5 For a Cu-catalyzed cross-coupling reaction involving t-BuMgCl and primary alkyl halides, see: Terao J, Todo H, Begum SA, Kuniyasu H, Kambe N. Angew. Chem. Int. Ed. 2007; 46: 2086
- 6 Luo X, Zhang H, Duan H, Liu Q, Zhu L, Zhang T, Lei A. Org. Lett. 2007; 9: 4571
- 7 Breitenfeld J, Vechorkin O, Corminboeuf C, Scopelliti R, Hu X. Organometallics 2010; 29: 3686
-
Examples of Ni-catalyzed cross-coupling of trans-β-bromostyrene and t-BuMgCl have been previously reported, see:
- 8a Hayashi T, Konishi M, Yokota K, Kumada M. Chem. Lett. 1980; 767
- 8b Nugent WA. Org. Lett. 2002; 4: 2133
- 9a Joshi-Pangu A, Wang C.-Y, Biscoe MR. J. Am. Chem. Soc. 2011; 133: 8478
- 9b Lohre C, Droge T, Wang C, Glorius F. Chem. Eur. J. 2011; 17: 6052
- 10 Modern Organonickel Chemistry . Tamaru Y. Wiley-VCH; Weinheim: 2005
-
In Cu(I)-catalyzed C–heteroatom cross-coupling reactions, it is likewise proposed that transmetallation precedes oxidative addition, see:
- 11a Jones GO, Liu P, Houk KN, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 6205
- 11b Yu H.-Z, Jiang Y.-Y, Fu Y, Liu L. J. Am. Chem. Soc. 2010; 132: 18078
- 12a Dible BR, Sigman MS, Arif AM. Inorg. Chem. 2005; 44: 3774
- 12b Miyazaki S, Koga Y, Matsumoto T, Matsubara K. Chem. Commun. 2010; 46: 1932
- 12c Zhang K, Conda-Sheridan M, Cooke SR, Louie J. Organometallics 2011; 30: 2546
- 12d Nagao S, Matsumoto T, Koga Y, Matsubara K. Chem. Lett. 2011; 40: 1036
-
Previous mechanistic studies of Ni-catalyzed processes involving tridentate nitrogen ligands also support a Ni(I)–Ni(III) catalytic cycle, see:
- 13a Lin X, Phillips DL. J. Org. Chem. 2008; 73: 3680
- 13b Jones GD, Martin JL, McFarland C, Allen OR, Hall RE, Haley AD, Brandon RJ, Konovalova T, Desrochers PJ, Pulay P, Vicic DA. J. Am. Chem. Soc. 2006; 128: 13175
- 13c Anderson TJ, Jones GD, Vicic DA. J. Am. Chem. Soc. 2004; 126: 8100
- 13d Phapale VB, Guisan-Ceinos M, Bunuel E, Cardenas DJ. Chem. Eur. J. 2009; 15: 12681
- 14a Holzer B, Hoffmann RW. Chem. Commun. 2003; 732
- 14b Hoffmann RW, Holzer B. Chem. Commun. 2001; 491
- 14c Hoffmann RW, Holzer B, Knopff O, Harms K. Angew. Chem. Int. Ed. 2000; 39: 3072
- 15 Boudier A, Bromm LO, Lotz M, Knochel P. Angew. Chem. Int. Ed. 2000; 39: 4414