4.8 Article

Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

Journal

ORGANIC LETTERS
Volume 16, Issue 6, Pages 1570-1573

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5000988

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Funding

  1. National Natural Science Foundation of China [21172143, 21172145, 21372152, 21232004]
  2. Nippon Chemical Industrial Co., Ltd.
  3. Shanghai Jiao Tong University (SJTU)
  4. Instrumental Analysis Center of SJTU

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C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

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