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Synfacts 2024; 20(08): 0817
DOI: 10.1055/s-0043-1775255
Metals in Synthesis

Photoinduced Palladium-Catalyzed 1,4-syn-Difunction­alization of Cyclic 1,3-Dienes

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Aliyaah J. M. Rahman
Liang Y, Bian T, Yadav K, Zhou Q, Zhou L, Sun R, Zhang Z. * Zhejiang Normal University, Jinhua, P. R. of China and University of Hawai’i at Mānoa, Honolulu, USA
Selective 1,4-syn-Addition to Cyclic 1,3-Dienes via Hybrid Palladium Catalysis.

ACS Cent. Sci. 2024;
10: 1191-1200
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Key words

1,4-syn-addition - cyclic 1,3-dienes - palladium catalysis - photocatalysis

Significance

A hybrid palladium-catalyzed protocol for the synthesis of 1,4-cis-substituted cyclic frameworks from 1,3-dienes, alkyl or aryl halides and a diverse array of nucleophiles is disclosed. This mild method features a broad substrate scope and exceptional 1,4-syn-addition selectivity (dr >20:1).


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Comment

The proposed radical-polar crossover mechanism with reverse facial selectivity is supported by density functional theory calculations and experimental studies such as radical trap and Stern–Volmer quenching experiments.


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Publication History

Article published online:
25 July 2024

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