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Rhodium(I)-catalyzed carboxylation of aryl- and alkenylboronic esters with CO2.
J Am Chem Soc. 2006 Jul 12; 128(27):8706-7.JA

Abstract

When the esters of arylboronic acids with 2,2-dimethylpropan-1,3-diol were treated with a catalytic amount of [Rh(OH)(cod)]2 in the presence of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60 degrees C under carbon dioxide atmosphere, the benzoic acid derivatives were obtained in good yields. Reactions of alkenylboronic esters also proceeded under similar conditions to give alpha,beta-unsaturated carboxylic acids. As these boronic esters are now easily available through coupling or direct borylation reactions, this method would be a useful method for the preparation of various functionalized aryl- and alkenyl-carboxylic acids.

Authors+Show Affiliations

Department of Chemistry, Tokyo Institute of Technology, O-Okayama, Meguro-ku, Tokyo 152-8551, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16819845

Citation

Ukai, Kazutoshi, et al. "Rhodium(I)-catalyzed Carboxylation of Aryl- and Alkenylboronic Esters With CO2." Journal of the American Chemical Society, vol. 128, no. 27, 2006, pp. 8706-7.
Ukai K, Aoki M, Takaya J, et al. Rhodium(I)-catalyzed carboxylation of aryl- and alkenylboronic esters with CO2. J Am Chem Soc. 2006;128(27):8706-7.
Ukai, K., Aoki, M., Takaya, J., & Iwasawa, N. (2006). Rhodium(I)-catalyzed carboxylation of aryl- and alkenylboronic esters with CO2. Journal of the American Chemical Society, 128(27), 8706-7.
Ukai K, et al. Rhodium(I)-catalyzed Carboxylation of Aryl- and Alkenylboronic Esters With CO2. J Am Chem Soc. 2006 Jul 12;128(27):8706-7. PubMed PMID: 16819845.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(I)-catalyzed carboxylation of aryl- and alkenylboronic esters with CO2. AU - Ukai,Kazutoshi, AU - Aoki,Masao, AU - Takaya,Jun, AU - Iwasawa,Nobuharu, PY - 2006/7/6/pubmed PY - 2007/9/11/medline PY - 2006/7/6/entrez SP - 8706 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 27 N2 - When the esters of arylboronic acids with 2,2-dimethylpropan-1,3-diol were treated with a catalytic amount of [Rh(OH)(cod)]2 in the presence of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60 degrees C under carbon dioxide atmosphere, the benzoic acid derivatives were obtained in good yields. Reactions of alkenylboronic esters also proceeded under similar conditions to give alpha,beta-unsaturated carboxylic acids. As these boronic esters are now easily available through coupling or direct borylation reactions, this method would be a useful method for the preparation of various functionalized aryl- and alkenyl-carboxylic acids. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16819845/Rhodium_I__catalyzed_carboxylation_of_aryl__and_alkenylboronic_esters_with_CO2_ L2 - https://doi.org/10.1021/ja061232m DB - PRIME DP - Unbound Medicine ER -