Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2022 Mar 29;12(16):9815-9820.
doi: 10.1039/d1ra09136k. eCollection 2022 Mar 25.

Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water

Ming Yang  1 , Yunzi Yu  1 , Wenxia Ma  1 , Yuqin Feng  1 , Gang Zhang  1 , Yaqi Wu  1 , Fanyu Zhou  1 , Yongsheng Yang  1 , Dezheng Liu  2
Affiliations

Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water

Ming Yang et al. RSC Adv. .

Abstract

A highly efficient and mild palladium-catalyzed hydroboration of unactivated internal alkynes in water is described. Both aryl- and alkyl-substituted alkynes proceeded smoothly within the reaction time to afford the desired vinylboronates in moderate to high yields. Bis (pinacolato) diboron was used to afford α- and β-hydroborated products in the presence of HOAc. These reactions showed high reactivities and tolerance, thus providing a promising method for the synthesis of alkenyl boron compounds.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Scheme 1
Scheme 1. Hydroboration of styrenes and selected applications of Arase–Hoshi hydroboration.15,17b–d
Scheme 2
Scheme 2. Proposed reaction mechanism.
See this image and copyright information in PMC

References

    1. For reviews, see:

    2. Boronic Acids-Preparation and Applications in Organic Synthesis and Medicine, ed. D. G. Hall, Wiley-VCH Publishers, Weinheim, Germany, 2005
    3. Beletskaya I. Moberg C. Chem. Rev. 2006;106:2320–2354. doi: 10.1021/cr050530j. - DOI - PubMed
    4. Beletskaya I. Moberg C. Chem. Rev. 1999;99:3435–3461. doi: 10.1021/cr9902594. - DOI - PubMed
    5. Irvine G. J. Lesley M. J. G. Marder T. B. Norman N. C. Rice C. R. Robins E. G. Roper W. R. Whittell G. R. Wright L. J. Chem. Rev. 1998;98:2685–2722. doi: 10.1021/cr9500085. - DOI - PubMed
    6. Miyaura N. Suzuki A. Chem. Rev. 1995;95:2457–2483. doi: 10.1021/cr00039a007. - DOI
    1. Irving A. M. Vogels C. M. Nikolcheva L. G. Edwards J. P. He X.-F. Hamilton M. G. Baerlocher M. O. Baerlocher F. J. Decken A. Westcott S. A. New J. Chem. 2003;27:1419–1424. doi: 10.1039/B304500E. - DOI
    2. Ito H. Kawakami C. Sawamura M. J. Am. Chem. Soc. 2005;127:16034–16035. doi: 10.1021/ja056099x. - DOI - PubMed
    3. Krautwald S. Bezdek M. J. Chirik P. J. J. Am. Chem. Soc. 2017;139:3868–3875. doi: 10.1021/jacs.7b00445. - DOI - PMC - PubMed

    1. For reviews, see:

    2. Suzuki A. in Organoboranes in syntheses, ACS symposium series 783, ed. P. V. Ramachandran and H. C. Brown, American Chemical Society, Washington, 2001, pp. 80–93, ch. 6
    3. Miyaura N. in Organoboranes in syntheses, ACS symposium series 783, ed. P. V. Ramachandran and H. C. Brown, American Chemical Society, Washington, 2001, pp. 94–107, ch. 7
    4. Palladium reagents and catalysts, ed. J. Tusiji, John Wiley & Sons Publishers, Chichester, England, 2014, pp. 218–227
    1. Wang M.-Y. Shi Z.-Z. Chem. Rev. 2020;120:7348–7398. doi: 10.1021/acs.chemrev.9b00384. - DOI - PubMed
    1. Boronic Acids, ed. D. G. Hall, Wiley-VCH Publishers, Weinheim, 2011
    2. Miyaura N. Suzuki A. Chem. Rev. 1995;95:2457. doi: 10.1021/cr00039a007. - DOI
    3. Kotha S. Lahiri K. Kashinath D. Tetrahedron. 2002;58:9633. doi: 10.1016/S0040-4020(02)01188-2. - DOI
    4. Molander G. A. Ellis N. Acc. Chem. Res. 2007;40:275. doi: 10.1021/ar050199q. - DOI - PubMed