Photoreductive 1,4-Dicarbofunctionalization of 1,3-Enynes with Organoiodides and Cyanoarenes via Halogen-Atom Transfer

Liang-Feng Yang; Liang Zeng; Yi-Lin Liu; Ming Hu; Jin-Heng Li

doi:10.1021/acs.orglett.4c02774

Photoreductive 1,4-Dicarbofunctionalization of 1,3-Enynes with Organoiodides and Cyanoarenes via Halogen-Atom Transfer

Org Lett. 2024 Sep 13;26(36):7661-7666. doi: 10.1021/acs.orglett.4c02774. Epub 2024 Aug 28.

Authors

Liang-Feng Yang^{1

2}, Liang Zeng², Yi-Lin Liu¹, Ming Hu², Jin-Heng Li^{1

2

3

4}

Affiliations

¹ Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Material, Institute of Organic Synthesis, Huaihua University, Huaihua 418000, China.
² State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
³ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
⁴ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 475004, China.

PMID: 39197044
DOI: 10.1021/acs.orglett.4c02774

Abstract

A photoreductive halogen-atom transfer (XAT) strategy for 1,4-dicarbofunctionalization of 1,3-enynes with organoiodides and cyanoarenes is disclosed, enabling access to functionalized allenes in a highly regio-, chemo-, and stereoselective manner. Upon the photoredox catalysis and the activation of Et₃N XAT agents, the mild conditions and high functional group tolerance of this protocol enable the formation of two C-C bonds, including a C(sp³)-C(sp³) bond and a C(sp²)-C(sp²) bond, in a single reaction step, and provides a general avenue to polysubstituted allenes and late-stage modification of bioactive compounds.