4.5 Article

Visible-Light-Induced Catalysis: A Regioselectivity Switch between [2+1] and [2+2] Cycloaddition of Diazocarbonyls with Olefins

Journal

SYNTHESIS-STUTTGART
Volume 54, Issue 17, Pages 3739-3752

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1786-6496

Keywords

photocatalysis; Rh-2(OAc)(4); cycloaddition; alpha-diazo compounds; switchable regioselectivity

Funding

  1. Taishan Scholars Construction Projects of Shandong [tsqn201812075]
  2. Natural Science Foundation of Shandong Province for Distinguished Young Scholars [ZR2020JQ07]
  3. Youth Innovation Science and Technology Plan of Colleges and Universities in Shandong Province [2019KJC003]
  4. Qingdao University of Science Technology

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Visible-light-promoted [2+1] and [2+2] cycloaddition reactions of diazocarbonyls with olefins have been developed, and the regioselectivity and reactivity could be controlled by the addition of Rh-2(OAc)(4) in the presence of Ir(ppy)(3) catalyst.
Visible-light-promoted [2+1] arid [2+2] cycloaddition reactions of diazocarbonyls with olefins have been developed, affording functionalized cyclopropanes and cyclobutanes, respectively. In visible-light catalysis of Ir(ppy)(3), a simple addition of Rh-2(OAc)(4) switches the regioselectivity from [2+1] to [2+2] cycloaddition with good reactivity and high regioselectivity.

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