Metal-Free Oxidative Decarbonylative [3+2] Annulation of Terminal Alkynes with Tertiary Alkyl Aldehydes toward Cyclopentenes

Hua-Xu Zou; Yang Li; Xu-Heng Yang; Jiannan Xiang; Jin-Heng Li

doi:10.1021/acs.joc.8b01130

Metal-Free Oxidative Decarbonylative [3+2] Annulation of Terminal Alkynes with Tertiary Alkyl Aldehydes toward Cyclopentenes

J Org Chem. 2018 Aug 3;83(15):8581-8588. doi: 10.1021/acs.joc.8b01130. Epub 2018 Jun 14.

Authors

Hua-Xu Zou^{1

2}, Yang Li^{1

2}, Xu-Heng Yang^{1

2}, Jiannan Xiang¹, Jin-Heng Li^{1

2

3}

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics , Hunan University , Changsha 410082 , China.
² Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle , Nanchang Hangkong University , Nanchang 330063 , China.
³ State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , China.

PMID: 29871487
DOI: 10.1021/acs.joc.8b01130

Abstract

A new metal-free oxidative decarbonylative [3+2] annulation of terminal alkynes with tertiary alkyl aldehydes is presented, which features broad substrate scope and excellent selectivity. The selectivity of this reaction toward cyclopentenes and indenes relies on the nature of the aldehyde substrates. While treatment of tertiary γ,δ-unsaturated aldehydes with common terminal alkynes assembles cyclopentenes, 2-methyl-2-arylpropanals succeed in accessing indenes.

Publication types

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