Lanthanoids in Hydroarylaminations: Yb(III)- and Tb(III)-Catalyzed Addition of Arylamines to Activated Olefins

Rajagopal Rajesh; Olencheri Karimpanakkal Sandhya; Sunilkumar Puthenpurackal Narayanan; Rajesh Kunjanpillai

doi:10.1055/a-2282-7702

Synthesis, Table of Contents

Synthesis 2024; 56(13): 2047-2058
DOI: 10.1055/a-2282-7702

paper

Lanthanoids in Hydroarylaminations: Yb(III)- and Tb(III)-Catalyzed Addition of Arylamines to Activated Olefins

Rajagopal Rajesh

^aDepartment of Chemistry, St. Albert’s College (Autonomous), Banerji Road, Kacheripady, Ernakulam, Kerala – 682018, India

,

Olencheri Karimpanakkal Sandhya

^bDepartment of Chemistry, MPMMSN Trust College, Shoranur, Palakkad, Kerala – 679122, India

,

Sunilkumar Puthenpurackal Narayanan

^cInstitute for Integrated Programmes and Research in Basic Sciences, Mahatma Gandhi University, Priyadarsini Hills, Athirampuzha, Kottayam, Kerala – 686560, India

,

Rajesh Kunjanpillai ∗

^aDepartment of Chemistry, St. Albert’s College (Autonomous), Banerji Road, Kacheripady, Ernakulam, Kerala – 682018, India

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Dedicated to the Late Prof. Ibrahim Ibnusaud, Founder Director, IIRBS, M. G. University, Kottayam, Kerala

Abstract

Michael-type hydroaminations of acrylonitrile, phenyl vinyl sulfone, and dimethyl maleate were realized using arylamines catalyzed independently by Yb(OTf)₃ and Tb(OTf)₃ to give the desired β-aminonitriles, β-amino sulfones, and dimethyl aspartates, respectively, in moderate to excellent yields. The reactions were carried out in toluene for Yb(OTf)₃ and in t-BuOMe for Tb(OTf)₃, all reactions were performed at 100 °C.

Key words

aza-Michael addition - β-amino acid derivatives - β-amino sulfones - lanthanide triflates - catalyst - terbium(III) triflate - ytterbium(III) triflate

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References

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