Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles

Shi-qi Zhang; Junqiang Xia

doi:10.1039/d4qo00085d

journal article Jan 01, 2024

Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles

Shi-qi Zhang Junqiang Xia

Organic Chemistry Frontiers Vol. 11 No. 9 pp. 2613-2623 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/d4qo00085d

Abstract

A Ru-catalyzed selective hydroacylation of acrylonitriles with aldehydes or alcohols towards β-ketonitriles is established. Glutaronitriles can be obtained through a one-step tandem hydroacylation and Michael addition of acrylonitrile and alcohols.

Topics

No keywords indexed for this article. Browse by subject →

References

127

[1]

Fleming J. Med. Chem. (2010) 10.1021/jm100762r

[2]

Prasad Biotechnol. Adv. (2010) 10.1016/j.biotechadv.2010.05.020

[3]

Wang RSC Med. Chem. (2021) 10.1039/d1md00131k

[4]

Yadav Phytochemistry (2023) 10.1016/j.phytochem.2022.113483

[5]

Shablykin Chem. Rec. (2023)

[6]

Paden J. Am. Chem. Soc. (1936) 10.1021/ja01303a038

[7]

Demko Angew. Chem., Int. Ed. (2002) 10.1002/1521-3773(20020617)41:12<2110::aid-anie2110>3.0.co;2-7

[8]

Elnagdi Synthesis (1984) 10.1055/s-1984-30717

[9]

Khidre Curr. Org. Chem. (2013) 10.2174/1385272811317040009

[10]

Wang J. Am. Chem. Soc. (2021) 10.1021/jacs.0c13273

[11]

Kiyokawa Synthesis (2018) 10.1055/s-0036-1589128

[12]

Dorsch J. Am. Chem. Soc. (1932) 10.1021/ja01346a047

[13]

Eby J. Am. Chem. Soc. (1957) 10.1021/ja01560a060

[14]

Katritzky J. Org. Chem. (2003) 10.1021/jo026796x

[15]

Ji Org. Lett. (2006) 10.1021/ol053164z

[16]

Mamuye Org. Biomol. Chem. (2015) 10.1039/c4ob02398f

[17]

Pienaar Beilstein J. Org. Chem. (2019) 10.3762/bjoc.15.287

[18]

Pyo Synthesis (2012) 10.1055/s-0032-1316760

[19]

Schranck Chem. – Eur. J. (2014) 10.1002/chem.201402893

[20]

Jensen J. Org. Chem. (2016) 10.1021/acs.joc.5b02897

[21]

Lee Tetrahedron Lett. (2016) 10.1016/j.tetlet.2015.12.050

[22]

Hu J. Am. Chem. Soc. (2021) 10.1021/jacs.1c00840

[23]

Zeng J. Org. Chem. (2021) 10.1021/acs.joc.0c02388

[24]

Park Acc. Chem. Res. (2008) 10.1021/ar700133y

[25]

Willis Chem. Rev. (2010) 10.1021/cr900096x

[26]

Yang Chem. Rev. (2015) 10.1021/cr500610p

[27]

Ghosh Org. Chem. Front. (2016) 10.1039/c6qo00023a

[28]

Guo Synlett (2018) 10.1055/s-0037-1610141

[29]

M.Fernández and M. C.Willis , in Rhodium Catalysis in Organic Synthesis , 2019 , pp. 63–84 10.1002/9783527811908.ch4

[30]

Davison Acc. Chem. Res. (2021) 10.1021/acs.accounts.0c00771

[31]

Sakai Tetrahedron Lett. (1972) 10.1016/s0040-4039(01)84569-x

[32]

Larock J. Am. Chem. Soc. (1980) 10.1021/ja00521a031

[33]

Bosnich Acc. Chem. Res. (1998) 10.1021/ar970095i

[34]

Kundu J. Am. Chem. Soc. (2005) 10.1021/ja0564416

[35]

Hoffman Angew. Chem., Int. Ed. (2011) 10.1002/anie.201104595

[36]

Yang J. Am. Chem. Soc. (2014) 10.1021/ja509919x

[37]

Johnson Org. Lett. (2015) 10.1021/acs.orglett.5b02559

[38]

Yang Angew. Chem., Int. Ed. (2017) 10.1002/anie.201611518

[39]

Yuan Tetrahedron (2019) 10.1016/j.tet.2018.11.057

[40]

Ken Bull. Chem. Soc. Jpn. (1999) 10.1246/bcsj.72.303

[41]

Coulter J. Am. Chem. Soc. (2010) 10.1021/ja107198e

[42]

Phan J. Am. Chem. Soc. (2010) 10.1021/ja107738a

[43]

von Delius J. Am. Chem. Soc. (2012) 10.1021/ja305593y

[44]

Murphy Angew. Chem., Int. Ed. (2014) 10.1002/anie.201309987

[45]

Guo J. Am. Chem. Soc. (2017) 10.1021/jacs.7b05427

[46]

Willis Angew. Chem., Int. Ed. (2004) 10.1002/anie.200352751

[47]

Moxham Angew. Chem., Int. Ed. (2006) 10.1002/anie.200603133

[48]

Osborne J. Am. Chem. Soc. (2008) 10.1021/ja8069133

[49]

Chaplin J. Am. Chem. Soc. (2012) 10.1021/ja211649a

[50]

Prades Angew. Chem., Int. Ed. (2015) 10.1002/anie.201503208

Showing 50 of 127 references

Metrics

7

Citations

127

References

Details

Published: Jan 01, 2024
Vol/Issue: 11(9)
Pages: 2613-2623
License: View

Authors

S

Shi-qi Zhang

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China; University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100049, China

J

Junqiang Xia

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China

Funding

National Natural Science Foundation of China Award: 22271296

Cite This Article

Shi-qi Zhang, Junqiang Xia (2024). Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles. Organic Chemistry Frontiers, 11(9), 2613-2623. https://doi.org/10.1039/d4qo00085d

Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles

You May Also Like