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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale |
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todo:paper_0022328X_v332_n1-2_p9_Vitale2023-10-03T14:31:33Z One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums Vitale, A.A. Doctorovich, F. Sbarbati Nudelman, N. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 |
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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. |
| format |
JOUR |
| author |
Vitale, A.A. Doctorovich, F. Sbarbati Nudelman, N. |
| spellingShingle |
Vitale, A.A. Doctorovich, F. Sbarbati Nudelman, N. One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums |
| author_facet |
Vitale, A.A. Doctorovich, F. Sbarbati Nudelman, N. |
| author_sort |
Vitale, A.A. |
| title |
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 |
| url |
http://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale |
| work_keys_str_mv |
AT vitaleaa onepotsynthesisofdiarylalkylcarbinolsandsubstitutedderivativesthroughcarbonmonoxideinsertionreactionsintoaryllithiums AT doctorovichf onepotsynthesisofdiarylalkylcarbinolsandsubstitutedderivativesthroughcarbonmonoxideinsertionreactionsintoaryllithiums AT sbarbatinudelmann onepotsynthesisofdiarylalkylcarbinolsandsubstitutedderivativesthroughcarbonmonoxideinsertionreactionsintoaryllithiums |
| _version_ |
1807322870176546816 |