Regioselective Generation of Aryllithiums from Substituted Bromobenzenes XC 6 H 4 Br (X = 4‐Br, 4‐I, 4‐CN, 2‐CN) | Zendy

Luliński Sergiusz | Zendy; Serwatowski Janusz | Zendy; Szczerbińska Magdalena | Zendy

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Regioselective Generation of Aryllithiums from Substituted Bromobenzenes XC 6 H 4 Br (X = 4‐Br, 4‐I, 4‐CN, 2‐CN)

Author(s) -

Luliński Sergiusz,

Serwatowski Janusz,

Szczerbińska Magdalena

Publication year - 2008

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.200701126

Subject(s) - chemistry , bromine , regioselectivity , deprotonation , medicinal chemistry , lithium (medication) , iodine , halogenation , organic chemistry , ion , catalysis , medicine , endocrinology

Selected activated bromobenzenes XC 6 H 4 Br (X = 4‐Br, 4‐I, 4‐CN, 2‐CN) were successfully deprotonated with lithium 2,2,6,6‐tetramethylpiperidide (LTMP) in THF at –80 °C. Thus, 2,5‐dibromo‐, 2‐bromo‐5‐iodo‐, 5‐bromo‐2‐cyano‐, and 3‐bromo‐2‐cyanophenyllithium were obtained as stable intermediates and could be converted by subsequent reactions into various functionalized derivatives with good yields. A competition of directing effects of bromine versus iodine and cyano groups is discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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