Volume 2018, Issue 3 pp. 306-315

Full Paper

Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols

Sudeshna Roy

Division of Chemical Biology and Medicinal Chemistry and the Center for Integrative Chemical Biology and Drug Discovery, UNC Eshelman School of Pharmacy, University of North Carolina, 27599 North Carolina, USA

Search for more papers by this author

Hashim F. Motiwala,

Hashim F. Motiwala

Department of Medicinal Chemistry, University of Kansas, Delbert M. Shankel Structural Biology Center, 2034 Becker Drive, West Campus, 66047 Lawrence, Kansas, USA

Search for more papers by this author

Karl M. Koshlap,

Karl M. Koshlap

Search for more papers by this author

Jeffrey Aubé,

Corresponding Author

Jeffrey Aubé

orcid.org/0000-0003-1049-5767

E-mail: [email protected]

https://pharmacy.unc.edu/news/directory/jaube/

Search for more papers by this author

Sudeshna Roy,

Sudeshna Roy

Search for more papers by this author

Hashim F. Motiwala,

Hashim F. Motiwala

Department of Medicinal Chemistry, University of Kansas, Delbert M. Shankel Structural Biology Center, 2034 Becker Drive, West Campus, 66047 Lawrence, Kansas, USA

Search for more papers by this author

Karl M. Koshlap,

Karl M. Koshlap

Search for more papers by this author

Jeffrey Aubé,

Corresponding Author

Jeffrey Aubé

orcid.org/0000-0003-1049-5767

E-mail: [email protected]

https://pharmacy.unc.edu/news/directory/jaube/

Search for more papers by this author

Dedicated to Al Padwa on the occasion of his 80th birthday

First published: 30 November 2017

https://doi.org/10.1002/ejoc.201701256

Citations: 10

Share a link

Email
Facebook
x
LinkedIn
Reddit
Wechat
Bluesky

Graphical Abstract

HFIP facilitates the mild catalytic hydroarylation of phenols to provide dihydrocoumarins using sub-stoichiometric amounts of acetyl chloride as catalyst.

Abstract

We report a catalytic hydroarylation method to convert phenols to dihydrocoumarins in hexafluoroisopropanol (HFIP) using acid generated from sub-stoichiometric amounts of acetyl chloride as catalyst. Attractive elements include easy set-up and isolation, and applicability to a range of phenols including natural product substrates.

Supporting Information

References

1C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura and Y. Fujiwara, Science, 2000, 287, 1992–1995.
10.1126/science.287.5460.1992
CASPubMedWeb of Science®Google Scholar
2Y. Yamamoto, Chem. Soc. Rev., 2014, 43, 1575–1600.
10.1039/C3CS60369E
CASPubMedWeb of Science®Google Scholar
3K. Li, L. N. Foresee and J. A. Tunge, J. Org. Chem., 2005, 70, 2881–2883.
10.1021/jo0477650
CASPubMedWeb of Science®Google Scholar
4J. R. S. Hoult and M. Payá, General Pharmacology: The Vascular System, 1996, 27, 713–722.
10.1016/0306-3623(95)02112-4
CASPubMedWeb of Science®Google Scholar
5B. M. Trost, F. D. Toste and K. Greenman, J. Am. Chem. Soc., 2003, 125, 4518–4526.
10.1021/ja0286573
CASPubMedWeb of Science®Google Scholar
6S. A. Stanley, T. Kawate, N. Iwase, M. Shimizu, A. E. Clatworthy, E. Kazyanskaya, J. C. Sacchettini, T. R. Ioerger, N. A. Siddiqi, S. Minami, J. A. Aquadro, S. S. Grant, E. J. Rubin and D. T. Hung, Proc. Natl. Acad. Sci. USA, 2013, 110, 11565–11570.
10.1073/pnas.1302114110
CASPubMedWeb of Science®Google Scholar
7J. R. Huh, E. E. Englund, H. Wang, R. Huang, P. Huang, F. Rastinejad, J. Inglese, C. P. Austin, R. L. Johnson, W. Huang and D. R. Littman, ACS Med. Chem. Lett., 2013, 4, 79–84.
10.1021/ml300286h
CASPubMedWeb of Science®Google Scholar
8X. Wu, L. Lan, D. M. Wilson, R. T. Marquez, W.-c. Tsao, P. Gao, A. Roy, B. A. Turner, P. McDonald, J. A. Tunge, S. A. Rogers, D. A. Dixon, J. Aubé and L. Xu, ACS Chem. Biol., 2015, 10, 1476–1484.
10.1021/cb500851u
CASPubMedWeb of Science®Google Scholar
9H. F. Motiwala, C. Fehl, S.-W. Li, E. Hirt, P. Porubsky and J. Aubé, J. Am. Chem. Soc., 2013, 135, 9000–9009.
10.1021/ja402848c
CASPubMedWeb of Science®Google Scholar
10H. F. Motiwala, M. Charaschanya, V. W. Day and J. Aubé, J. Org. Chem., 2016, 81, 1593–1609.
10.1021/acs.joc.5b02764
CASPubMedWeb of Science®Google Scholar
11H. F. Motiwala, R. H. Vekariya and J. Aubé, Org. Lett., 2015, 17, 5484–5487.
10.1021/acs.orglett.5b02851
CASPubMedWeb of Science®Google Scholar
12R. H. Vekariya and J. Aubé, Org. Lett., 2016, 18, 3534–3537.
10.1021/acs.orglett.6b01460
CASPubMedWeb of Science®Google Scholar
13Hammett constants are obtained from from J. E. Leffler and E. Grunwald, in: Rates and Equilibria of Organic Reactions, 1963.
Google Scholar
14J. Wencel-Delord and F. Glorius, Nat. Chem., 2013, 5, 369–375.
10.1038/nchem.1607
CASPubMedWeb of Science®Google Scholar
15K. Y. Koltunov, S. Walspurger and J. Sommer, Eur. J. Org. Chem., 2004, 4039–4047.
10.1002/ejoc.200400313
CASWeb of Science®Google Scholar
16K. Li and J. A. Tunge, J. Comb. Chem., 2008, 10, 170–174.
10.1021/cc700150q
CASPubMedWeb of Science®Google Scholar
17A. R. Jagdale and A. Sudalai, Tetrahedron Lett., 2007, 48, 4895–4898.
10.1016/j.tetlet.2007.05.059
CASWeb of Science®Google Scholar
18K. Yoshida, T. Yamaguchi, T. Adachi, T. Otomo, D. Matsuo, T. Takamuku and N. Nishi, J. Chem. Phys., 2003, 119, 6132–6142.
10.1063/1.1602070
CASWeb of Science®Google Scholar
19I. Colomer, C. Batchelor-McAuley, B. Odell, T. J. Donohoe and R. G. Compton, J. Am. Chem. Soc., 2016, 138, 8855–8861.
10.1021/jacs.6b04057
CASPubMedWeb of Science®Google Scholar

Citing Literature

Volume2018, Issue3

January 23, 2018

Pages 306-315

Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Related

Information