Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel-Crafts reaction

Yafang Dong, Masahiko Sakai, Kazuto Fuji, Kohei Sekine, Yoichiro Kuninobu

Research output: Contribution to journalArticlepeer-review

Abstract

We have developed a catalytic synthetic method to prepare phenoxasilins. A borane-catalyzed double sila-Friedel-Crafts reaction between amino group-containing diaryl ethers and dihydrosilanes can be used to prepare a variety of phenoxasilin derivatives in good to excellent yields. The optimized reaction conditions were also applicable for diaryl thioethers to afford their corresponding six-membered silacyclic products. The gram-scale synthesis of a representative bis(dimethylamino)phenoxasilin and the transformation of its amino groups have also been demonstrated.

Original languageEnglish
Pages (from-to)409-414
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - Mar 17 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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