4 years ago

Synthesis of Biphenylenes and Their Higher Homologues by Cyclization of Aryne Derivatives

Synthesis of Biphenylenes and Their Higher Homologues by Cyclization of Aryne Derivatives
Sheng-Li Wang, Yao-Ting Wu, Ming-Lun Pan, Wei-Siang Su
This investigation demonstrates that a series of biphenylenes can be easily prepared from their corresponding halobiphenyls by the cyclization of in situ generated 2′,3′-didehydro-2-lithiobiphenyls at low temperature. Two remarkable advantages of this synthetic method include 1) the lack of any need for transition-metal catalysts or reagents in the cyclization, and 2) the ability to obtain C1-functionalized products by treating the reaction intermediate 1-lithiobiphenylene with an electrophilic reagent. π-Extended derivatives, such as benzobiphenylenes, dibenzobiphenylene, linear/angular [3]phenylenes, and biphenyleno[2,3-b]biphenylenes, were synthesized similarly using suitable biaryls or teraryls. Biphenylenes can be easily and efficiently obtained at low temperature by the organolithium-mediated cyclization of halobiphenyls via an aryne intermediate. This synthetic protocol provides an advantage for the direct and controlled functionalization at the C1 position.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708892

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