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Synfacts 2025; 21(07): 690
DOI: 10.1055/a-2601-5693
Metals in Synthesis

Iridium-Catalyzed Hydroalkenylation of Alkenes to Access γ-Substituted Chiral Acrylamides

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Sergiu Bicic 
Wang K, Tian K-Y, Wang X-N, Chen J-H, Fan C, Zhou Q-L *. Nankai University, Tianjin, P. R. China
Ligand Enabled Iridium-Catalyzed Enantioselective Hydroalkenylation of α‑Olefins and Styrenes with Acrylamides.

J. Am. Chem. Soc. 2025;
147: 11639-11646
DOI: 10.1021/jacs.4c18412
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Keywords

acrylamides - alkenes - hydroalkenylation - iridium catalysis

Significance

An iridium-catalyzed, ligand-enabled regio- and enantioselective hydroalkenylation of unactivated olefins and styrene derivatives with acrylamides is reported. Various γ-substituted chiral acrylamides were obtained in high yields with excellent branched regioselectivity and enantioselectivity.


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Comment

Mechanistic studies and DFT calculations support the shown catalytic cycle. The use of a new spiro diphosphite ligand was the key to achieving high enantioselectivities. This SPINOL-derived ligand forms a semicage-like cavity around the active center of the catalyst, thereby effectively controlling the orientation of the substrate during coordination with the metal.


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Publication History

Article published online:
23 June 2025

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