4.8 Article

Synthesis of Structurally Diverse Allylsilanes via Copper-Catalyzed Regiodivergent Hydrosilylation of 1,3-Dienes

Journal

ORGANIC LETTERS
Volume 23, Issue 12, Pages 4736-4742

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01455

Keywords

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Funding

  1. National Natural Science Foundation of China [21871240]
  2. State Key Laboratory of Elemento-organic Chemistry Nankai University [202001]
  3. Fundamental Research Funds for the Central Universities [WK2060000017]

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Novel copper-catalyzed regiodivergent hydrosilylation reactions have been developed, allowing highly selective control of 1,2- and 1,4-hydrosilylation reactions of substituted 1,3-dienes by varying the catalytic systems. Additionally, the first successful 1,4-hydrosilylation reaction of 2-aryl-substituted 1,3-dienes with diphenylsilane was achieved, providing convenient and efficient methods for synthesizing structurally diverse allylsilanes.
Unprecedented copper-catalyzed regiodivergent hydrosilylation reactions of substituted 1,3-dienes with hydrosilanes have been developed. The 1,2- and 1,4-hydrosilylations of 1-(hetero)aryl-substituted 1,3-dienes were highly selectively controlled via variation of the catalytic systems. Meanwhile, the 1,4-hydrosilylation reaction of 2-aryl-substituted 1,3-dienes with diphenylsilane was also successfully realized for the first time. These methods provide convenient and efficient approaches for the synthesis of structurally diverse allylsilanes.

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