Oxoammonium‐Mediated Allylsilane–Ether Coupling Reaction. Issue 15 (23rd March 2021)

• Record Type: Journal Article
• Authors: Carlet, Federica; Bertarini, Greta; Broggini, Gianluigi; Pradal, Alexandre; Poli, Giovanni
• Is Part Of: European journal of organic chemistry. Issue 15(2021)
• Page Start: 2162
• Page End: 2168
• Publication Date: 2021-03-23
• Subjects: Allylation -- Benzyl ethers -- Cinnamyl ethers -- C(sp3)−H functionalization -- Oxoammonium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100026
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new C(sp 3 )−H functionalization reaction consisting of the oxidative α‐allylation of allyl‐ and benzyl‐ methyl ethers has been developed. The C−C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners. Abstract : An oxoammonium‐mediated α‐C(sp 3 ) allylation of allyl‐ and benzyl ethers using allylsilanes as nucleophilic partners is disclosed. This new C−C bond forming C−H activation process allows to obtain the corresponding coupled products in moderate to good yields.