4.8 Article

Dehydrative Allylation of Alkenyl sp2 C-H Bonds

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ORGANIC LETTERS
卷 23, 期 11, 页码 4368-4373

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01309

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资金

  1. National Natural Science Foundation of China [21702108]
  2. Natural Science Foundation of Jiangsu Province, China [BK20160977]
  3. Six Talent Peaks Project in Jiangsu Province [YY-033]

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A cooperative catalytic system was designed and successfully applied to the dehydrative allylation of alkenes, with a novel C-OH bond cleavage method playing a crucial role. Various alkenes and allylic alcohols with diverse functional groups can be efficiently incorporated into the desired cross-coupling reaction, yielding 1,4-dienes with moderate to high yields and high selectivity.
We designed a cooperative catalytic system by combining commercially available Ca(NTf2)PF6 and Pd(PPh3)(4) to address the dehydrative allylation of alkenyl sp(2) C-H bonds in an environmentally benign manner. A novel C-OH bond cleavage method was found to be crucial for this practical protocol. A variety of alkenes and allylic alcohols equipped with wide-spectrum functional groups can be successfully incorporated into the desired cross-coupling, affording 1,4-dienes with moderate to excellent yields and high stereo- and regioselectivity.

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