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(E)-N-(pyren-1-ylmethylene)benzenamine: efficient promoter for additive-free palladium catalyzed aerobic oxidative coupling of arylboronic acids and terminal alkynes

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A highly productive protocol for the synthesis of internal alkynes by the carbon–carbon cross-coupling reactions of electronically different arylboronic acids with substituted phenylacetylenes was described by employing (E)-N-(pyren-1-ylmethylene)benzenamine with Pd(OAc)2. The influence of reaction parameters such as solvent, base and reaction temperature in this carbon–carbon cross-coupling reaction was also investigated. The substrate scope could be expanded to electron-poor alkynes, for which the conventional Sonogashira reaction gives poor yields. Moderate to excellent yield was obtained in the oxidative Sonogashira-type coupling reaction.

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Acknowledgements

Dr. J. Lakshmipraba gratefully acknowledges the financial support from Department of Science & Technology (DST), New Delhi, India, for the Women Scientists Scheme-A (WOS-A) (Ref No. SR/WOS-A/CS-59/2017). The use of the NMR facility at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India, is also thankfully acknowledged. We also acknowledge the Management of Bishop Heber College for the facilities provided through DST-FIST, DBT-STAR Scheme, UGC-CE and Heber Analytical Instrumentation Facility (HAIF), Bishop Heber College.

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Correspondence to Jagadeesan Lakshmipraba.

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Lakshmipraba, J., Prabhu, R.N. & Dhayabaran, V.V. (E)-N-(pyren-1-ylmethylene)benzenamine: efficient promoter for additive-free palladium catalyzed aerobic oxidative coupling of arylboronic acids and terminal alkynes. Chem. Pap. 74, 3661–3669 (2020). https://doi.org/10.1007/s11696-020-01156-8

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  • DOI: https://doi.org/10.1007/s11696-020-01156-8

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