Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines

Wen-Bo Shen; Xin-Yu Xiao; Qing Sun; Bo Zhou; Xin-Qi Zhu; Juan-Zhu Yan; Xin Lu; Long-Wu Ye

doi:10.1002/anie.201610042

Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines

Angew Chem Int Ed Engl. 2017 Jan 9;56(2):605-609. doi: 10.1002/anie.201610042. Epub 2016 Dec 9.

Authors

Wen-Bo Shen¹, Xin-Yu Xiao¹, Qing Sun¹, Bo Zhou¹, Xin-Qi Zhu¹, Juan-Zhu Yan¹, Xin Lu¹, Long-Wu Ye^{1

2}

Affiliations

¹ Collaborative Innovation Center of Chemistry for Energy Materials, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

PMID: 27936302
DOI: 10.1002/anie.201610042

Abstract

Platinum-catalyzed formal [5+2] and [4+2] annulations of isoxazoles with heterosubstituted alkynes enabled the atom-economical synthesis of valuable 1,3-oxazepines and 2,5-dihydropyridines, respectively. Importantly, this Pt catalysis not only led to unique reactivity dramatically divergent from that observed under Au catalysis, but also proceeded via unprecedented α-imino platinum carbene intermediates.

Keywords: annulation; heterocycles; homogeneous catalysis; platinum; ynamides.

Publication types

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