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Reactivity of 3‐Substituted Fluorobenzenes in Palladium‐ Catalysed Direct Arylations with Aryl Bromides
Author(s) -
Yan Tao,
Zhao Liqin,
He Mian,
Soulé JeanFrançois,
Bruneau Christian,
Doucet Henri
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400038
Subject(s) - chemistry , palladium , nitrile , regioselectivity , aryl , medicinal chemistry , nitro , reactivity (psychology) , bromide , transmetalation , catalysis , organic chemistry , alkyl , medicine , pathology , alternative medicine
The influence of both electron‐withdrawing and electron‐donating substituents such as nitro, nitrile, chloro, bromo and methoxy at C‐3 on fluorobenzenes for their palladium‐catalysed direct C‐2 arylation has been explored. With electron‐withdrawing substituents, the reaction proceeds nicely using 2–4 mol% of an air‐stable palladium complex and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic system; and in general, a very regioselective arylation at C‐2 was observed. Moreover, a variety of substituents on the aryl bromide coupling partner, such as benzoyl, formyl, nitro, nitrile, chloro and methyl, and also heteroaryl bromides were tolerated.