Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 7
Submit an article Journal homepage
394
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Iron-catalyzed boration of allylic alcohols with H3BO3 as an additive

Yuhan ZhouState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-1860-8669View further author information
ORCID Icon,
Huan WangState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaORCID Iconhttp://orcid.org/0000-0001-5792-7841View further author information
ORCID Icon,
Yang LiuState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaORCID Iconhttp://orcid.org/0000-0002-5860-1437View further author information
ORCID Icon,
Yilong ZhaoState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaORCID Iconhttp://orcid.org/0000-0001-7938-8973View further author information
ORCID Icon,
Chunxia ZhangState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaORCID Iconhttp://orcid.org/0000-0002-5197-4679View further author information
ORCID Icon &
Jingping QuState Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. ChinaORCID Iconhttp://orcid.org/0000-0002-7576-0798View further author information
ORCID Icon
Pages 795-801 | Received 09 Dec 2017, Published online: 26 Feb 2018

References

  • (a) Barrio, P.; Rodríguez, E.; Fustero, S. Chem. Rec. 2016, 16, 2046–2060; (b) Deng, H.-P.; Wang, D.; Szabό, K. J. J. Org. Chem. 2015, 80, 3343–3348; (c) Farmer, J. L.; Hunter, H. N.; Organ, M. G. J. Am. Chem. Soc. 2012, 134, 17470–17473.
  • (a)Diner, C.; Szabό, K. J. J. Am. Chem. Soc. 2017, 139, 2–14; (b) Neeve, E. C.; Geier, S. J.; Mkhalid, I. A. I.; Westcott, S. A. Chem. Rev. 2016, 116, 9091–9161; (c) Luo, Y.; Roy, I. D.; Madec, A. G. E.; Lam, H. W. Angew. Chem. Int. Ed. 2014, 53, 4186–4190 (d) Chen, J. L. Y.; Aggarwal, V. K. Angew. Chem. Int. Ed. 2014, 53, 10992–10996.
  • (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207–2293; (b) Lachance, H.; Hall, D. G. Org. React. 2008, 73, 1–341.
  • Ishiyama, T.; Ahiko, T.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889–6892.
  • (a) Ito, H.; Kunii, S.; Sawamura, M. Nat. Chem. 2010, 2, 972–976; (b) Yamamoto, E.; Takenouchi, Y.; Ozaki, T.; Miya, T.; Ito, H. J. Am. Chem. Soc. 2014, 136, 16515–16521; (c) Guzman-Martinez, A.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10634–10637; (d) Qiu, Y.; Yang, B.; Zhu, C.; Bäckvall, J.-E. Angew. Chem. Int. Ed. 2016, 55, 6520–6524; (e) Zhou, Q.; Srinivas, H. D.; Zhang, S.; Watson, M. P. J. Am. Chem. Soc. 2016, 138, 11989–11995; (f) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856–14857; (g) Park, J. K.; Lackey, H. H.; Ondrusek, B. A.; McQuade, T. J. Am. Chem. Soc. 2011, 133, 2410–2413.
  • (a) Olsson, V. J.; Sebelius, S.; Selander, N.; Szabό, K. J. J. Am. Chem. Soc. 2006, 128, 4588–4589; (b) Selander, N.; Szabό, K. J. J. Org. Chem. 2009, 74, 5695–5698; (c) Selander, N.; Paasch, J. R.; Szabό, K. J. J. Am. Chem. Soc. 2011, 133, 409–411; (d) Raducan, M.; Alam, R.; Szabό, K. J. Angew. Chem. Int. Ed. 2012, 51, 13050–13053; (e) Larsson, J. M.; Szabό, K. J. J. Am. Chem. Soc. 2013, 135, 443–455; (f) Biggs, R. A.; Lambadaris, M.; Ogilvie, W. W. Tetrahedron Lett. 2014, 55, 6085–6087.
  • (a) Miralles, N.; Alam, R.; Szabό, K. J.; Fernández, E. Angew. Chem. Int. Ed. 2016, 55, 4303–4307; (b) Harada, K.; Nogami, M.; Hirano, K.; Kurauchi, D.; Kato, H.; Miyamoto, K.; Saito, T.; Uchiyama, M. Org. Chem. Front. 2016, 3, 565–569; (c) Mao, L.; Szabό, K. J.; Marder, T. B. Org. Lett. 2017, 19, 1204–1207; (d) Xuan, Q.; Wei, Y.; Chen, J.; Song, Q. Org. Chem. Front. 2017, 4, 1220–1223 (e) Corberán, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2011, 50, 7079–7082.
  • (a) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467–4483; (b) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929–7967; (c) Lu, X.; Lu, L.; Sun, J. J. Mol. Catal. 1987, 41, 245–251; (d) Masuyama, Y.; Kagawa, M.; Kurusu, Y. Chem. Lett. 1995, 24, 1121–1122; (e) Yang, S.-C.; Hung, C.-W. J. Org. Chem. 1999, 64, 5000–5001; (f) Yang, S.-C.; Tsai, Y.-C. Organometallics 2001, 20, 763–770; (g) Sakamoto, M.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1996, 69, 1065–1078; (h) Yamashita, Y.; Gopalarathnam, A.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7508–7509; (i) Lang, S. B.; Locascio, T. M.; Tunge, J. A. Org. Lett. 2014, 16, 4308–4311.
  • (a) Kimura, M.; Futamata, M.; Shibata, K.; Tamaru, Y. Chem. Commun. 2003, 234–235; (b) Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592–4593; (c) Lu, X.; Jiang, X.; Tao, X. J. Organomet. Chem. 1998, 344, 109–118; (d) Starý, I.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 1993, 34, 179–182; (e) Abidi, A.; Oueslati, Y.; Rezgui, F. Synth. Commun. 2016, 46, 1916–1923.
  • (a) Liu, Y.; Zhou, Y.; Wang, H.; Qu, J. RSC Adv. 2015, 5, 73705–73713; (b) Liu, Y.; Zhou, Y.; Zhao, Y.; Qu, J. Org. Lett. 2017, 19, 946–949; (c) Zhou, Y.; Wang, H.; Liu, Y.; Zhao, Y.; Zhang, C.; Qu, J. Org. Chem. Front. 2017, 4, 1580–1585.
  • (a) Dang, L.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 4443–4454; (b) Bonet, A.; Pubill-Ulldemolins, C.; Bo, C.; Gulyás, H.; Fernández, E. Angew. Chem. Int. Ed. 2011, 50, 7158–7161; (c) Bedford, R. B.; Brenner, P. B.; Carter, E.; Gallagher, T.; Murphy, D. M.; Pye, D. R. Organometallics 2014, 33, 5940–5943; (d) Wu, J. Y.; Moreau, B.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 12915–12917.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.