A Catecholaldimine-Based NiII-Complex as an Effective Catalyst for the Direct Conversion of Alcohols to trans-Cinnamonitriles and Aldehydes

Vivek Sharma; Kailas Arjun Chavan; Ghanshyam Mali; Dipanjana Sarkar; Prem Lama; Moumita Majumder; Rohan D Erande; Ramesh K Metre

doi:10.1021/acs.joc.2c03067

A Catecholaldimine-Based Ni^II-Complex as an Effective Catalyst for the Direct Conversion of Alcohols to trans-Cinnamonitriles and Aldehydes

J Org Chem. 2023 Jun 2;88(11):7448-7453. doi: 10.1021/acs.joc.2c03067. Epub 2023 May 8.

Authors

Vivek Sharma¹, Kailas Arjun Chavan¹, Ghanshyam Mali¹, Dipanjana Sarkar¹, Prem Lama², Moumita Majumder³, Rohan D Erande¹, Ramesh K Metre¹

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Jodhpur, Jodhpur 342030, Rajasthan, India.
² CSIR-Indian Institute of Petroleum, Haridwar Road, Mokhampur, Dehradun 248005, India.
³ Department of Metallurgical and Materials Engineering, Indian Institute of Technology Jodhpur, Jodhpur 342030, India.

PMID: 37155715
DOI: 10.1021/acs.joc.2c03067

Abstract

A nickel(II) complex [Ni(HL)₂] 1 was synthesized by treatment of a new catecholaldimine-based ligand with NiCl₂·6H₂O in methanol at room temperature. Complex 1 showed excellent catalytic activity where aromatic and heterocyclic alcohols were rapidly converted into trans-cinnamonitrile in a one-pot manner via oxidative olefination in the presence of KOH. The potential of the disclosed catalyst and the results obtained for the direct conversion of alcohols to two different functionalities (trans-cinnamonitrile and aldehydes) are well supported by DFT studies.