Hypervalent Iodine-Mediated Intramolecular trans-Aminocarboxylation and Oxoaminocarboxylation of Alkynes: Divergent Cascade Annulations of Isocoumarins under Metal-Free Conditions

Xiang Zhang; Wenjuan Hou; Daisy Zhang-Negrerie; Kang Zhao; Yunfei Du

doi:10.1021/acs.orglett.5b02611

Hypervalent Iodine-Mediated Intramolecular trans-Aminocarboxylation and Oxoaminocarboxylation of Alkynes: Divergent Cascade Annulations of Isocoumarins under Metal-Free Conditions

Org Lett. 2015 Nov 6;17(21):5252-5. doi: 10.1021/acs.orglett.5b02611. Epub 2015 Oct 12.

Authors

Xiang Zhang¹, Wenjuan Hou¹, Daisy Zhang-Negrerie¹, Kang Zhao¹, Yunfei Du^{1

2}

Affiliations

¹ School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, P. R. China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.

PMID: 26458214
DOI: 10.1021/acs.orglett.5b02611

Abstract

An exclusive trans-aminocarboxylation and oxoaminocarboxylation of diarylalkynes were realized through hypervalent iodine-mediated cascade annulations under metal-free conditions, leading to divergent assembly of fused or spiro polycyclic heterocycles with a dosage of the hypervalent iodine oxidant. The mechanisms for the formation of both products are proposed.

Publication types

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

MeSH terms

Alkynes / chemistry*
Catalysis
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Iodine / chemistry*
Isocoumarins / chemistry*
Lewis Acids / chemistry
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Alkynes
Heterocyclic Compounds, 4 or More Rings
Isocoumarins
Lewis Acids
Spiro Compounds
Iodine