Mild Synthesis of Sterically Congested Alkyl Aryl Ethers | Zendy

Erik Lindstedt | Zendy; Elin Stridfeldt | Zendy; Berit Olofsson | Zendy

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Mild Synthesis of Sterically Congested Alkyl Aryl Ethers

Author(s) -

Erik Lindstedt,

Elin Stridfeldt,

Berit Olofsson

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01975

Subject(s) - chemistry , steric effects , alkyl , aryl , allylic rearrangement , tertiary alcohols , organic chemistry , primary (astronomy) , alcohol , combinatorial chemistry , medicinal chemistry , catalysis , physics , astronomy

An efficient and transition-metal-free method is presented to access tertiary alkyl aryl ethers by arylation of tertiary alcohols with ortho-substituted diaryliodonium salts. The scope covers cyclic and acyclic aliphatic, benzylic, allylic, and propargylic tertiary alcohols as well as primary and secondary fluorinated alcohols. The methodology gives access to alkyl aryl ethers of previously unprecedented steric congestion. Furthermore, the versatility of the developed procedure was demonstrated by arylation of the pro-drug mestranol.

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