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Synfacts 2022; 18(11): 1199
DOI: 10.1055/s-0042-1753023
Metals in Synthesis

Palladium-Catalyzed Butafulvene Synthesis

Contributor(s):
Mark Lautens
,
Alexa Torelli
Huang X, Chen B.-Z, Li P, Ji D.-W, Liu J, Zheng H, Yang S.-N, Hu Y.-C, Wan B, Hu X.-P, Fu C, Huang Y, Zheng J, *, Chen Q.-A, *, Ma S. * Zhejiang University and Dalian Institute of Chemical Physics, P. R. of China
Palladium-Catalysed Construction of Butafulvenes.

Nat. Chem. 2022;
14: 1185-1192
DOI: 10.1038/s41557-022-01017-9
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Key words

palladium catalysis - small-ring synthesis - butafulvenes

Significance

A palladium-catalyzed coupling of propargylic carbonates or bromides has been developed to synthesize butafulvene derivatives. Two sets of mild reaction conditions are reported to access either symmetrical butafulvenes or unsymmetrical products when coupling with allenylic boronate or in-situ-prepared allenyl-indium reagents.


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Comment

Primary propargyl carbonates were unreactive; however, in-situ prepared allenyl-indium reagents could be used as an alternative to access symmetrical terminal butafulvenes. Intermediate tracking and control experiments shed light on a potential reaction pathway, indicating that bisallene C undergoes palladium-catalyzed cycloisomerization to generate the product.


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Publication History

Article published online:
18 October 2022

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