Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

The first Pd-catalyzed multicomponent reaction of aryl iodides, alkenyl bromides, and strained alkenes has been developed, which allowed us to synthesize a variety of multisubsituted olefins in yields of 45–96% with excellent stereoselectivity. The configuration of the product was controlled by the...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-04, Vol.83 (8), p.4441-4454
Main Authors: Hao, Tao-Tao, Liang, Hao-Ran, Ou-Yang, Ying-Han, Yin, Chang-Zhen, Zheng, Xue-Li, Yuan, Mao-Lin, Li, Rui-Xiang, Fu, Hai-Yan, Chen, Hua
Format: Article
Language:English
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Summary:The first Pd-catalyzed multicomponent reaction of aryl iodides, alkenyl bromides, and strained alkenes has been developed, which allowed us to synthesize a variety of multisubsituted olefins in yields of 45–96% with excellent stereoselectivity. The configuration of the product was controlled by the configuration of the alkenyl bromides. Moreover, this practical methodology employing readily available substrates was found to be tolerant to a wide range of functional groups. Fifty six examples of highly stereoselective tri- or tetrasubstituted olefins have been successfully synthesized via this methodology. Most of the synthesized tetrasubstituted olefins are good aggregation-induced emission (AIE) luminogens.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00150