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Synthesis 2017; 49(17): 3925-3930
DOI: 10.1055/s-0036-1588986
DOI: 10.1055/s-0036-1588986
special topic
Large-Scale Cobalt-Catalyzed Cross-Couplings of Functionalized Bench-Stable Arylzinc Pivalates with (Hetero)Aryl and Alkenyl Halides
Further Information
Publication History
Received: 13 February 2017
Accepted after revision: 09 March 2017
Publication Date:
18 April 2017 (online)
Published as part of the Special Topic Cobalt in Organic Synthesis
Abstract
A robust and scalable CoCl2-catalyzed cross-coupling between functionalized arylzinc pivalates and various electron-poor (hetero)aryl and alkenyl halides is reported.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588986.
- Supporting Information
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References
- 1a Miyaura N. Cross-Coupling Reactions. A Practical Guide. Springer; Berlin: 2002
- 1b Metal-Catalyzed Cross-Coupling Reactions. Diederich F. de Meijere A. Wiley-VCH; Weinheim: 2004
- 1c Modern Drug Synthesis. Li JJ. Johnson DS. Wiley-VCH; Weinheim: 2010
- 1d Organotransition Metal Chemistry . Hartwig JF. University Science Books; Sausalito: 2010
- 2a Noguchi H. Hojo K. Suginome M. J. Am. Chem. Soc. 2007; 129: 758
- 2b Lee SJ. Gray KC. Paek JS. Burke MD. J. Am. Chem. Soc. 2008; 130: 466
- 2c Knapp DM. Gillis EP. Burke MD. J. Am. Chem. Soc. 2009; 131: 6961
- 3a Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 3b Miyaura N. Yamada K. Suginome H. Suzuki A. J. Am. Chem. Soc. 1985; 107: 972
- 3c Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
- 4a Molander GA. Biolatto B. J. Org. Chem. 2003; 68: 4302
- 4b Molander GA. Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
- 5a Wender PA. Hilinski MK. Mayweg AV. W. Org. Lett. 2005; 7: 79
- 5b Campbell MG. Ritter T. Org. Process Res. Dev. 2014; 18: 474
- 6 O’Donovan MR. Mee CD. Fenner S. Teasdale A. Phillips DH. Mutat. Res. 2011; 724: 1
- 7 Haas D. Hammann JM. Greiner R. Knochel P. ACS Catal. 2016; 6: 1540
- 8 NMR experiments and crystallographic data showed that the structure of these zinc reagents is RZnX·Mg(OPiv)2·LiCl. However, for the sake of clarity, we have named these reagents RZnOPiv, see: Hernán-Gómez A. Herd E. Hevia E. Kennedy AR. Knochel P. Koszinowski K. Manolikakes SM. Mulvey RE. Schnegelsberg C. Angew. Chem. Int. Ed. 2014; 53: 2706
- 9a Bernhardt S. Manolikakes G. Kunz T. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9205
- 9b Stathakis CI. Bernhardt S. Quint V. Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9428
- 9c Colombe JR. Bernhardt S. Stathakis C. Buchwald SL. Knochel P. Org. Lett. 2013; 15: 5754
- 9d Stathakis CI. Manolikakes SM. Knochel P. Org. Lett. 2013; 15: 1302
- 9e Manolikakes SM. Ellwart M. Stathakis CI. Knochel P. Chem. Eur. J. 2014; 20: 12289
- 10 World market prices: Pd ca. 22700 €/kg, Co ca. 35 €/kg; http://www.infomine.com/; retrieved February 2017.
- 11a Handbook on the Toxicology of Metals . Friberg L. Nordberg GF. Vouk VB. Elsevier; Amsterdam: 1986
- 11b Hughes MN. Comprehensive Coordination Chemistry . Vol. 6. Wilkinson G. Gillard RD. McCleverty JA. Pergamon; Oxford: 1987: 643-648
- 11c Nickel and the Skin: Absorption, Immunology, Epidemiology, and Metallurgy . Hostynek JJ. Maibach HI. CRC; Boca Raton: 2002
- 12 Prices retrieved from Alfa Aesar; February 2017.
- 13a Egorova KS. Ananikov VP. Angew. Chem. Int. Ed. 2016; 55: 12150
- 13b Moore W. Hysell D. Hall L. Campbell K. Stara J. Environ. Health Perspect. 1975; 10: 63
- 14a Xu W. Yoshikai N. Angew. Chem. Int. Ed. 2016; 55: 12731
- 14b Yan J. Yoshikai N. ACS Catal. 2016; 6: 3738
- 14c Wang H. Moselage M. Gonzalez MJ. Ackermann L. ACS Catal. 2016; 6: 2705
- 14d Zell D. Bu Q. Feldt M. Ackermann L. Angew. Chem. Int. Ed. 2016; 55: 7408
- 14e Nicolas L. Izquierdo E. Angibaud P. Stansfield I. Meerpoel L. Reymond S. Cossy J. J. Org. Chem. 2013; 78: 11807
- 14f Barre B. Gonnard L. Campagne R. Reymond S. Marin J. Ciapetti P. Brellier M. Guerinot A. Cossy J. Org. Lett. 2014; 16: 6160
- 14g Gonnard L. Guerinot A. Cossy J. Chem. Eur. J. 2015; 21: 12797
- 14h Corpet M. Bai X.-Z. Gosmini C. Adv. Synth. Catal. 2014; 356: 2937
- 14i Cai Y. Qian X. Gosmini C. Adv. Synth. Catal. 2016; 358: 2427
- 14j Pal S. Chowdhury S. Rozwadowski E. Auffrant A. Gosmini C. Adv. Synth. Catal. 2016; 358: 2431
- 14k Cahiez G. Chaboche C. Duplais C. Giulliani A. Moyeux A. Adv. Synth. Catal. 2008; 350: 1484
- 14l Cahiez G. Chaboche C. Duplais C. Moyeux A. Org. Lett. 2009; 11: 277
- 14m Kobayashi T. Ohmiya H. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2008; 130: 11276
- 14n Murakami K. Yorimitsu H. Oshima K. Chem. Eur. J. 2010; 16: 7688
- 14o Gensch T. Klauck FJ. R. Glorius F. Angew. Chem. Int. Ed. 2016; 55: 11287
- 14p Lerchen A. Vásquez-Céspedes S. Glorius F. Angew. Chem. Int. Ed. 2016; 55: 3208
- 15 Hammann JM. Lutter FH. Haas D. Knochel P. Angew. Chem. Int. Ed. 2017; 56: 1082
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