ortho ‐Lithiation Reactions of  O ‐(3, n ‐Dihalophenyl)  N , N ‐Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3, n ‐Trihalophenol Derivatives | Zendy

Feberero Claudia | Zendy; Velasco Rocío | Zendy; Sanz Roberto | Zendy

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ortho ‐Lithiation Reactions of O ‐(3, n ‐Dihalophenyl) N , N ‐Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3, n ‐Trihalophenol Derivatives

Author(s) -

Feberero Claudia,

Velasco Rocío,

Sanz Roberto

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600933

Subject(s) - chemistry , metalation , regioselectivity , medicinal chemistry , stereochemistry , tandem , sequence (biology) , organolithium compounds , chemical synthesis , combinatorial chemistry , organic chemistry , catalysis , deprotonation , ion , biochemistry , materials science , composite material , in vitro

New dihalosalicylamides and trihalophenol derivatives have been synthesized from easily available O ‐(3, n ‐dihalophenyl) N , N ‐diethylcarbamates by using a directed ortho ‐metalation (D o M) strategy. The o ‐lithiation reactions with s BuLi take place regioselectively at the doubly activated C‐2 position, which demonstrates the ability of O ‐carbamates as directed metalating groups. In addition, highly functionalized arylnitriles were accessed from organolithium intermediates by using a tandem transnitrilation/S N Ar reaction sequence.

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