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Org Lett. 2016 Jul 01;18(13):3290-3. doi: 10.1021/acs.orglett.6b01605. Epub 2016 Jun 22.

Selective Rhodium-Catalyzed Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes with a Tetraphosphoramidite Ligand.

Organic letters

Zongpeng Zhang, Qian Wang, Caiyou Chen, Zhengyu Han, Xiu-Qin Dong, Xumu Zhang

Affiliations

  1. College of Chemistry and Molecular Sciences, Wuhan University , Wuhan, Hubei 430072, P. R. China.
  2. Department of Chemistry, South University of Science and Technology of China , Shenzhen, Guangdong 518055, P. R. China.

PMID: 27333272 DOI: 10.1021/acs.orglett.6b01605

Abstract

A tetraphosphoramidite ligand was successfully applied to a Rh-catalyzed hydroformylation of various symmetrical and unsymmetrical alkynes to afford corresponding α,β-unsaturated aldehyde products in good to excellent yields (up to 97% yield). Excellent chemo- and regioselectivities and high activities (up to 20 000 TON) were achieved. The corresponding α,β-unsaturated aldehyde products can be transformed into many useful and important organic molecules, such as indenamine derivatives and lukianol pyrroles. This great performance makes the hydroformylation of alkynes highly practical with great potential.

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