Palladium‐Catalyzed Skeletal Rearrangement of Substituted 2‐Silylaryl Triflates via 1,5‐C−Pd/C−Si Bond Exchange

Author:

Hayashi Daigo1,Tsuda Tomohiro1,Shintani Ryo12ORCID

Affiliation:

1. Division of Chemistry Department of Materials Engineering Science Graduate School of Engineering Science Osaka University Toyonaka Osaka 560-8531 Japan

2. Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI) Osaka University Suita Osaka 565-0871 Japan

Abstract

AbstractA palladium‐catalyzed skeletal rearrangement of 2‐(2‐allylarylsilyl)aryl triflates has been developed to give highly fused tetrahydrophenanthrosilole derivatives via unprecedented 1,5‐C−Pd/C−Si bond exchange. The reaction pathways can be switched toward 4‐membered ring‐forming C(sp2)−H alkylation by tuning the reaction conditions to give completely different products, fused dihydrodibenzosilepin derivatives, from the same starting materials. The inspection of the reaction conditions revealed the importance of carboxylates in promoting the C−Pd/C−Si bond exchange.

Publisher

Wiley

Subject

General Medicine

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