3 years ago

RhI-Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones

Tao Xu, Tianwen Sun, Yuna Zhang, Guangbin Dong, Yafei Wang, Yuting Qin, Bo Qiu
Herein we describe the first example of a Rh-catalyzed carboacylation/aromatization cascade of a C=O bond via C−C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and subsequently the resulting two Rh−C bonds add across a C=O bond followed by elimination, providing a unique strategy to access a multi-substituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained in good yields. Mechanistic study shows a tricyclic lactone-containing intermediate was isolated and advanced to a benzofuran analogue through elimination under the standard conditions. Further utility of this methodology into the total synthesis of C13-deOH-viniferifuran and C13-deOH-diptoindonesin G was achieved in 8 and 9 steps, respectively.

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

DOI: 10.1002/anie.201713179

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