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

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.

SUBMITTER: Dong Y

PROVIDER: S-EPMC7113548 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Dong Yafang Y Sakai Masahiko M Fuji Kazuto K Sekine Kohei K Kuninobu Yoichiro Y

Beilstein journal of organic chemistry 20200317

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 a ...[more]

PMID: 32273904

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