4.7 Article

Regiospecific synthesis of distally chlorinated ketones via C-C bond cleavage of cycloalkanols

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 3, Issue 2, Pages 227-232

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5qo00368g

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Funding

  1. Soochow University
  2. National Natural Science Foundation of China [21402134]
  3. Natural Science Foundation of Jiangsu [BK20140306]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
  5. Natural Science Foundation of China [NSFC 21302133]

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A variety of distally Csp(3)-chlorinated ketones are synthesized with good regioselectivities via silver-catalyzed ring opening of cycloalkanols under mild reaction conditions. The reaction uses only routine, inexpensive reagents and can be scaled up to gram quantities. A novel radical-mediated C-C bond cleavage/C-Cl bond formation is proposed.

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