One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums

The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction parti...

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Publicado: 1987
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022328X_v332_n1-2_p9_Vitale
http://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_0022328X_v332_n1-2_p9_Vitale
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spelling paper:paper_0022328X_v332_n1-2_p9_Vitale2023-06-08T14:49:39Z One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction particularly useful for the synthesis of alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols. The procedure can also be adapted to afford substituted cyclic ethers. If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful synthetic intermediates. With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields. © 1987. 1987 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022328X_v332_n1-2_p9_Vitale http://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction particularly useful for the synthesis of alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols. The procedure can also be adapted to afford substituted cyclic ethers. If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful synthetic intermediates. With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields. © 1987.
title One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
spellingShingle One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
title_short One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
title_full One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
title_fullStr One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
title_full_unstemmed One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
title_sort one-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
publishDate 1987
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022328X_v332_n1-2_p9_Vitale
http://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale
_version_ 1768542068497448960

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