Straightforward Synthesis of Oligopyrroles through a Regioselective SNAr Reaction of Pyrroles and Halogenated Boron Dipyrrins

A novel stepwise and regioselective nucleophilic aromatic substitution (SNAr) reaction of halogenated boron dipyrrins (BODIPYs) with pyrroles has been developed under mild conditions with no catalyst needed and shown to be diversity oriented. The resultant pyrrole-substituted BODIPYs are interesting...

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Published in:Organic letters 2014-04, Vol.16 (7), p.1952-1955
Main Authors: Jiang, Ting, Zhang, Ping, Yu, Changjiang, Yin, Jian, Jiao, Lijuan, Dai, En, Wang, Jun, Wei, Yun, Mu, Xiaolong, Hao, Erhong
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Language:eng ; jpn
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container_end_page 1955
container_issue 7
container_start_page 1952
container_title Organic letters
container_volume 16
creator Jiang, Ting
Zhang, Ping
Yu, Changjiang
Yin, Jian
Jiao, Lijuan
Dai, En
Wang, Jun
Wei, Yun
Mu, Xiaolong
Hao, Erhong
description A novel stepwise and regioselective nucleophilic aromatic substitution (SNAr) reaction of halogenated boron dipyrrins (BODIPYs) with pyrroles has been developed under mild conditions with no catalyst needed and shown to be diversity oriented. The resultant pyrrole-substituted BODIPYs are interesting red and near-infrared (NIR) fluorescent dyes with absorption maxima up to 733 nm. Removal of the BF2 protecting group of the 3-pyrrole or 3,5-dipyrrole-substituted BODIPYs provides a facial entry to oligopyrroles with direct 2,2′-bipyrrole linkages.
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title Straightforward Synthesis of Oligopyrroles through a Regioselective SNAr Reaction of Pyrroles and Halogenated Boron Dipyrrins
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