Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines

Yong Wang; Li-Juan Song; Xinhao Zhang; Jianwei Sun

doi:10.1002/anie.201603889

Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines

Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9704-8. doi: 10.1002/anie.201603889. Epub 2016 Jul 6.

Authors

Yong Wang^{1

2}, Li-Juan Song³, Xinhao Zhang⁴, Jianwei Sun^{5

6}

Affiliations

¹ Department of Chemistry, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR, China.
² HKUST Shenzhen Research Institute, Shenzhen, 518057, China.
³ Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
⁴ Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, China. [email protected].
⁵ Department of Chemistry, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR, China. [email protected].
⁶ HKUST Shenzhen Research Institute, Shenzhen, 518057, China. [email protected].

PMID: 27381408
DOI: 10.1002/anie.201603889

Abstract

A metal-free trimolecular [2+2+2] cycloaddition of internal ynamides and nitriles for de novo synthesis of fully substituted pyridines is disclosed. With the versatile Brønsted acid catalyst HNTf2 , the mild intermolecular cyclotrimerization process proceeds with complementary chemoselectivity and excellent regioselectivity.

Keywords: Brønsted acid; cycloaddition; cyclotrimerization; heterocycles; reaction mechanisms.

Publication types

Research Support, Non-U.S. Gov't