Domino C–H Activation Reactions through Proximity Effects. Issue 40 (9th October 2018)

• Record Type: Journal Article
• Authors: Lotz, Florian; Kahle, Klaus; Kangani, Mehrnoush; Senthilkumar, Soundararasu; Tietze, Lutz F.
• Is Part Of: European journal of organic chemistry. Issue 40(2018)
• Page Start: 5562
• Page End: 5569
• Publication Date: 2018-10-09
• Subjects: Carbopalladation -- C–H Activation -- Domino reactions -- Cross‐coupling -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801289
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Proximity effects permit C–H activation reactions without directing groups. Here competitive reactions of selected substrates were investigated which allow a domino‐carbopalladation/Mizoroki–Heck reaction and a domino‐carbopalladation/C–H activation reaction. In the Pd‐catalyzed transformation of the enantio‐ and diastereopure alkyne8a the tetra‐substituted alkenes10 and11 were formed almost exclusively through a domino carbopalladation/Mizoroki–Heck reaction. In contrast, the diastereomer8c only led to the acenaphthylenes12c and13c through a domino carbopalladation/C–H activation reaction. Moreover, in the reaction of20, 24 and27 containing a naphthyl moiety only the tetra‐substituted alkenes23, 25 /26 and28 /29, respectively were obtained, whereas in the reaction of34, containing a phenanthrene moiety, compound37 was the only product, formed via a C–H activation reaction. Abstract : Proximity effects allow C–H‐activation reactions without directing groups in competition with domino‐carbopalladation or Mizoroki–Heck reactions. Vinly–Pd species can be assumed as intermediates, which either react with a double bond or a naphthyl or phenanthryl moiety.