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Cobalt-Catalyzed Intermolecular [2+2+2] Cycloaddition of Nitriles and Alkynes: Facile Synthesis of Polyarylpyridines and Their Mechanochemical Cyclodehydrogenation to Nitrogen-Containing Polyaromatics

preprint
submitted on 21.12.2020, 02:50 and posted on 22.12.2020, 13:07 by Chang-Sheng Wang, Qiao Sun, Felipe Garcia, Chen Wang, Naohiko Yoshikai
Simple, inexpensive and robust cobalt-based catalytic systems for the [2+2+2] cycloaddition between unactivated nitriles and diarylacetylenes are reported. The present systems tolerate a broad range of aryl and alkyl nitriles and cyanamides as well as various di(hetero)arylacetylenes, allowing for the facile preparation of diverse polyarylated pyridines. Mechanochemistry-enabled multifold cyclodehydrogenation of tetra- and pentaarylpyridine is demonstrated to achieve the synthesis of nitrogen-containing polycyclic aromatic compounds having hitherto unprecedented skeletons.

Funding

Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2016-T2-2-043 to N.Y.) and Tier 1 (RG114/18 to N.Y.)

Zhejiang Provincial Natural Science Foundation of China (Grant LY18B020007 to C.W.)

A*STAR (AME IRG A1783c0003 to F.G.)

History

Email Address of Submitting Author

nyoshikai@ntu.edu.sg

Institution

Nanyang Technological University

Country

Singapore

ORCID For Submitting Author

0000-0002-8997-3268

Declaration of Conflict of Interest

The authors declare that there is no conflict of interest.

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