Ytterbium(II) Complex-Catalyzed Selective Single and Double Hydrophosphination of 1,3-Enynes

Bing Jing; Cheng Zhu; Haibin Song; Jianfeng Li; Chunming Cui

doi:10.1002/chem.202401234

Ytterbium(II) Complex-Catalyzed Selective Single and Double Hydrophosphination of 1,3-Enynes

Chemistry. 2024 May 7:e202401234. doi: 10.1002/chem.202401234. Online ahead of print.

Authors

Bing Jing¹, Cheng Zhu¹, Haibin Song¹, Jianfeng Li¹, Chunming Cui²

Affiliations

¹ Nankai University, State Key Laboratory of Elemento-Organic Chemistry, CHINA.
² Nankai University, Institute of Elemento-Organic Chemistry, 94 Weijin Road, 300071, Tianjin, CHINA.

PMID: 38712548
DOI: 10.1002/chem.202401234

Abstract

1,3-Enynes with the conjugated alkene and alkyne moieties are attractive building blocks in synthetic chemistry. However, neither 4,1-hydrophosphination nor dihydrophosphination of 1,3-enynes has been reported. In this paper, the divalent ytterbium and calcium amide complexes supported by silaimine-functionalized cyclopentadiene ligands (C5Me4-Si(L)=NR) were developed, which successfully catalyzed the efficient single and double hydrophosphination of 1,3-enynes with diarylphosphines. These two hydrophosphination reactions selectively produced homoallenyl phosphines and (E)-propenylene diphosphines, respectively. This work demonstrated the potential of hemilabile silaimine-Cp ligands in supporting the efficient and selective rare- and alkaline-earth catalysts.

Keywords: rare-earth metal, alkaline-earth metal, hydrophosphination, enyne, allene.