journal article Jan 01, 2018

Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones

View at Publisher Save 10.1039/c8cc01059e
Abstract
A dehydrogenative coupling reaction of cyclic enones with thiophenes through palladium-catalyzed C–H functionalization is reported herein. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenols are also demonstrated.
Topics

No keywords indexed for this article. Browse by subject →

References
79
[1]
Jia Acc. Chem. Res. (2001) 10.1021/ar000209h
[2]
Jia Science (2000) 10.1126/science.287.5460.1992
[3]
Jia Org. Lett. (1999) 10.1021/ol991148u
[4]
Fujiwara J. Am. Chem. Soc. (1969) 10.1021/ja01053a047
[5]
Moritani Tetrahedron Lett. (1967) 10.1016/s0040-4039(00)90648-8
[6]
Zhou Chem. – Eur. J. (2014) 10.1002/chem.201303670
[7]
Kozhushkov Chem. Sci. (2013) 10.1039/c2sc21524a
[8]
Arockiam Chem. Rev. (2012) 10.1021/cr300153j
[9]
Le Bras Chem. Rev. (2011) 10.1021/cr100209d
[10]
Satoh Chem. – Eur. J. (2010) 10.1002/chem.201001363
[11]
Dams Angew. Chem., Int. Ed. (2003) 10.1002/anie.200351524
[12]
Yokota J. Am. Chem. Soc. (2003) 10.1021/ja028903a
[13]
Radomkit Angew. Chem., Int. Ed. (2014) 10.1002/anie.201309982
[14]
Kwiatkowski Org. Lett. (2011) 10.1021/ol201275h
[15]
Kehrli Chem. – Eur. J. (2010) 10.1002/chem.201000471
[16]
Chen J. Am. Chem. Soc. (2009) 10.1021/ja9045839
[17]
Jimenez Bioorg. Med. Chem. Lett. (2008) 10.1016/j.bmcl.2008.05.059
[18]
Moreno-Dorado Tetrahedron (1999) 10.1016/s0040-4020(99)00328-2
[19]
Boibessot J. Med. Chem. (2016) 10.1021/acs.jmedchem.6b00580
[20]
Diao J. Am. Chem. Soc. (2013) 10.1021/ja4031648
[21]
Izawa Angew. Chem., Int. Ed. (2013) 10.1002/anie.201209457
[22]
Simon Angew. Chem., Int. Ed. (2012) 10.1002/anie.201200698
[23]
Quideau Angew. Chem., Int. Ed. (2011) 10.1002/anie.201000044
[24]
Wang Nature (2017) 10.1038/nature24632
[25]
Hartwig ACS Cent. Sci. (2016) 10.1021/acscentsci.6b00032
[26]
Ying Org. Lett. (2014) 10.1021/ol4033804
[27]
Kubota Org. Lett. (2012) 10.1021/ol300281p
[28]
Kuhl Angew. Chem., Int. Ed. (2012) 10.1002/anie.201203269
[29]
Zhang J. Am. Chem. Soc. (2009) 10.1021/ja900327e
[30]
Muzart Eur. J. Org. Chem. (2010) 10.1002/ejoc.201000278
[31]
Gao Chem. Sci. (2012) 10.1039/c1sc00661d
[32]
Diao Chem. Sci. (2012) 10.1039/c1sc00724f
[33]
Diao J. Am. Chem. Soc. (2011) 10.1021/ja206575j
[34]
Shvo J. Org. Chem. (1998) 10.1021/jo980112x
[35]
Weinstein Org. Lett. (2016) 10.1021/acs.orglett.6b01611
[36]
Shi Org. Lett. (2013) 10.1021/ol400198q
[37]
Jordan-Hore Org. Lett. (2012) 10.1021/ol300794a
[38]
Gottumukkala Chem. – Eur. J. (2012) 10.1002/chem.201200694
[39]
Kikushima J. Am. Chem. Soc. (2011) 10.1021/ja200664x
[40]
Lin Org. Lett. (2010) 10.1021/ol100767u
[41]
Nishitaka Chem. Lett. (2007) 10.1246/cl.2007.1442
[42]
Gini Org. Lett. (2005) 10.1021/ol052222d
[43]
Nishikata Angew. Chem., Int. Ed. (2003) 10.1002/anie.200350888
[44]
Chung ChemCatChem (2015) 10.1002/cctc.201500079
[45]
Gigant Chem. – Eur. J. (2014) 10.1002/chem.201402063
[46]
Moon Angew. Chem., Int. Ed. (2012) 10.1002/anie.201206610
[47]
Liang Green Chem. (2016) 10.1039/c6gc02674e
[48]
Zhang Chem. Sci. (2015) 10.1039/c5sc01044f
[49]
Walker Org. Lett. (2013) 10.1021/ol400539h
[50]
Gottumukkala J. Org. Chem. (2011) 10.1021/jo101942f

Showing 50 of 79 references

Metrics
21
Citations
79
References
Details
Published
Jan 01, 2018
Vol/Issue
54(29)
Pages
3668-3671
License
View
Funding
National Natural Science Foundation of China Award: 21502106
Natural Science Foundation of Shanxi Province Award: 201701D221028
Cite This Article
Zhen-Kang Wen, Ting-Ting Song, Yu-Fang Liu, et al. (2018). Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones. Chemical Communications, 54(29), 3668-3671. https://doi.org/10.1039/c8cc01059e
Related

You May Also Like