Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(17): 3895-3904
DOI: 10.1055/s-0036-1588996
DOI: 10.1055/s-0036-1588996
special topic
Hydroboration and Diboration of Internal Alkynes Catalyzed by a Well-Defined Low-Valent Cobalt Catalyst
Further Information
Publication History
Received: 13 February 2017
Accepted after revision: 17 March 2017
Publication Date:
06 April 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201717/lookinside/thumbnails/ss-2017-c0089-st_10-1055_s-0036-1588996-1.jpg)
Published as part of the Special Topic Cobalt in Organic Synthesis
Abstract
The use of a simple well-defined low-valent cobalt(I) catalyst [HCo(PMe3)4] capable of performing the regio- and stereoselective hydroboration of internal alkynes is reported. Extension to the diboration of internal alkynes is also related using the same reaction conditions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588996.
- Supporting Information
-
References
- 1a Boronic Acids . Hall DG. Wiley-VCH; Weinheim: 2011
- 1b Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
- 1c Miyaura N. Top. Curr. Chem. 2002; 219: 11
- 1d Kotha S. Lahiri K. Kashinath D. Tetrahedron 2002; 58: 9633
- 1e Molander GA. Ellis N. Acc. Chem. Res. 2007; 40: 275
- 1f Neeve E. Geier S. Mkhalid I. Westcott S. Marder T. Chem. Rev. 2016; 116: 9091
- 1g Yoshida H. ACS Catal. 2016; 6: 1799
- 2a Beletskaya I. Moberg C. Chem. Rev. 1999; 99: 3435
- 2b Beletskaya I. Moberg C. Chem. Rev. 2006; 106: 2320
- 2c Miyaura N. Bull. Chem. Soc. Jpn. 2008; 81: 1535
- 2d Ohmura T. Suginome M. Bull. Chem. Soc. Jpn. 2009; 82: 29
- 2e Suginome M. Chem. Rec. 2010; 10: 348
- 2f Oestreich M. Hartmann E. Mewald M. Chem. Rev. 2013; 113: 402
- 2g Cuenca AB. Shishido R. Ito H. Fernández E. Chem. Soc. Rev. 2017; 46: 415
- 3a Yun J. Asian J. Org. Chem. 2013; 2: 1016
- 3b Fujihara T. Semba K. Terao J. Tsuji Y. Catal. Sci. Technol. 2014; 4: 1699
- 3c Barbeyron R. Benedetti E. Cossy J. Vasseur J.-J. Arseniyadis S. Smietana M. Tetrahedron 2014; 70: 8431
- 3d Semba K. Fujihara T. Terao J. Tsuji Y. Tetrahedron 2015; 71: 2183
- 3e Yoshida H. Chem. Rec. 2016; 16: 419
- 4a Haberberger M. Enthaler S. Chem. Asian J. 2013; 8: 50
- 4b Greenhalgh MD. Thomas SP. Chem. Commun. 2013; 49: 11230
- 4c Rawat VS. Sreedhar B. Synlett 2014; 25: 1132
- 4d Khan A. Asiri AM. Kosa SA. Garcia H. Grirrane A. J. Catal. 2015; 329: 401
- 5a Obligacion JV. Neely JM. Yazdani AN. Pappas I. Chirik PJ. J. Am. Chem. Soc. 2015; 137: 5855
- 5b Zuo Z. Huang Z. Org. Chem. Front. 2016; 3: 434
- 6 Xi T. Lu Z. ACS Catal. 2017; 7: 1181
- 7a Dai C. Stringer G. Corrigan JF. Taylor NJ. Marder TB. Norman NC. J. Organomet. Chem. 1996; 513: 273
- 7b Adams CJ. Baber RA. Batsanov AS. Bramham G. Charmant JP. H. Haddow MF. Howard JA. K. Lam WH. Lin Z. Marder TB. Norman NC. Orpen AG. Dalton Trans. 2006; 1370
- 8 Ventre S. Simon C. Rekhroukh F. Malacria M. Amatore M. Aubert C. Petit M. Chem. Eur. J. 2013; 19: 5830
- 9a Ventre S. Derat E. Amatore M. Aubert C. Petit M. Adv. Synth. Catal. 2013; 355: 2584
- 9b Fallon BJ. Derat E. Amatore M. Aubert C. Chemla F. Ferreira F. Perez-Luna A. Petit M. J. Am. Chem. Soc. 2015; 137: 2448
- 9c Fallon BJ. Garsi J.-B. Derat E. Amatore M. Aubert C. Petit M. ACS Catal. 2015; 5: 7493
- 9d Fallon BJ. Derat E. Amatore M. Aubert C. Chemla F. Ferreira F. Perez-Luna A. Petit M. Org. Lett. 2016; 18: 2292
- 9e Fallon BJ. Corcé V. Amatore M. Aubert C. Chemla F. Ferreira F. Perez-Luna A. Petit M. New J. Chem. 2016; 40: 9912
- 10 Rivera-Hernández A. Fallon BJ. Ventre S. Simon C. Tremblay M. Gontard G. Derat E. Amatore M. Aubert C. Petit M. Org. Lett. 2016; 18: 4242
- 11 The strong electron-withdrawing effect of the ester may also explain the observed selectivity.
- 12 Nagao K. Ohmiya H. Sawamura M. Org. Lett. 2015; 17: 1304
- 13 Preliminary 1H NMR study shows the disappearance of the characteristic Co–H signal when mixing HCo(PMe3)4 and HBPin, and a gas evolution suggesting a reductive elimination of H2. However, we did not manage to isolate the new species formed.
- 14 Ansell MB. Navarro O. Spencer J. Coord. Chem. Rev. 2017; 336: 54
- 15 Yoshida H. Kawashima S. Takemoto Y. Okada K. Ohshita J. Takaki K. Angew. Chem. Int. Ed. 2012; 51: 235
- 16 Nakagawa N. Hatakeyama T. Nakamura M. Chem. Eur. J. 2015; 21: 4257
- 17 Nagashima Y. Hirano K. Takita R. Uchiyama M. J. Am. Chem. Soc. 2014; 136: 8532
- 18 Still WC. Kahn M. Mitra AJ. J. Org. Chem. 1978; 43: 2923
- 19 Kim HR. Yun J. Chem. Commun. 2011; 47: 2943
- 20 Grirrane A. Corma A. Garcia H. Chem. Eur. J. 2011; 17: 2467
- 21 Morinaga A. Nagao K. Ohmiya H. Sawamura M. Angew. Chem. Int. Ed. 2015; 54: 15859
- 22 Chen Q. Zhao J. Ishikawa Y. Asao N. Yamamoto Y. Jin T. Org. Lett. 2013; 15: 5766
- 23 Jiao J. Hyodo K. Hu H. Nakajima K. Nishihara Y. J. Org. Chem. 2014; 79: 285
- 24 Mkhalid IA. I. Coapes RB. Edes SN. Coventry DN. Souza FE. S. Thomas RL. Hall JJ. Bi S.-W. Lin Z. Marder TB. Dalton Trans. 2008; 8: 1055