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In situ preparation of rhodium/n-heterocyclic carbene complexes and use for addition of arylboronic acids to aldehydes

✍ Scribed by Rafet Kilinçarslan; Engin Çetinkaya; Bekir Çetinkaya; Murat Yiǧit; İsmail Özdemir


Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
324 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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The in situ prepared three component system [RhCl(COD)]~2~/imidazolidinium salts (2, 4) and KOBu^t^ catalyses the addition of phenylboronic acid to sterically hindered aldehydes affording the corresponding arylated secondary alcohols in good yields. Four novel 1,3‐dialkylimidazolidinium (2‐4) salts as NHC precursors were synthesized from N,N′‐dialkylethylenediamine.


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## Abstract The Rh complex **1a** of (__S__,__S__)‐1‐(2‐diphenylphosphanylnaphthalen‐1‐yl)‐3‐(2‐isopropylphenyl)‐4,5‐diphenylimidazolidin‐2‐ylidene was found to promote enantioselective conjugate additions of arylboronic acids to enones and α,β‐unsaturated esters with up to 98% yield and>99% ee. Pr