Direct oxidative C(sp3)H cyanation of secondary benzylic ethers

A practical and efficient oxidative CH cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described for the first time. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans for the synthesis of isochromans bearin...

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Bibliographic Details
Published in:Chinese chemical letters 2019-06, Vol.30 (6), p.1241-1243
Main Authors: Wang, Zehua, Mao, Ying, Guan, Honghao, Cao, Min, Hua, Jing, Feng, Lei, Liu, Lei
Format: Article
Language:English
Subjects:
C[sbnd]H functionalization
Cyanation
Oxidation
Secondary ether
Tertiary ether synthesis
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Summary:A practical and efficient oxidative CH cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described for the first time. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans for the synthesis of isochromans bearing α-aryl α-cyano substituent patterns. [Display omitted] Current studies on the oxidative CH functionalization of benzylic ethers for CC forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a practical and efficient oxidative CH cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans, facilely furnishing a library of isochromans bearing α-aryl α-cyano substituent patterns for further diversification and bioactive small molecule identification.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.03.019