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Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2.
J Am Chem Soc. 2012 Jul 25; 134(29):11900-3.JA

Abstract

The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl(2), bis(imino)pyridine 6 (1 mol %), CO(2) (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO(2)).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Greenhalgh MD
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom.
Thomas SP
No affiliation info available

MeSH

AlkenesCarbon DioxideCarboxylic AcidsCatalysisHydrocarbons, AromaticIronStereoisomerismStyrene

Pub Type(s)

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

Language

eng

PubMed ID

22779807

Citation

Greenhalgh, Mark D., and Stephen P. Thomas. "Iron-catalyzed, Highly Regioselective Synthesis of Α-aryl Carboxylic Acids From Styrene Derivatives and CO2." Journal of the American Chemical Society, vol. 134, no. 29, 2012, pp. 11900-3.
Greenhalgh MD, Thomas SP. Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2. J Am Chem Soc. 2012;134(29):11900-3.
Greenhalgh, M. D., & Thomas, S. P. (2012). Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2. Journal of the American Chemical Society, 134(29), 11900-3. https://doi.org/10.1021/ja3045053
Greenhalgh MD, Thomas SP. Iron-catalyzed, Highly Regioselective Synthesis of Α-aryl Carboxylic Acids From Styrene Derivatives and CO2. J Am Chem Soc. 2012 Jul 25;134(29):11900-3. PubMed PMID: 22779807.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2. AU - Greenhalgh,Mark D, AU - Thomas,Stephen P, Y1 - 2012/07/13/ PY - 2012/7/12/entrez PY - 2012/7/12/pubmed PY - 2012/12/10/medline SP - 11900 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 29 N2 - The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl(2), bis(imino)pyridine 6 (1 mol %), CO(2) (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO(2)). SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22779807/Iron_catalyzed_highly_regioselective_synthesis_of_α_aryl_carboxylic_acids_from_styrene_derivatives_and_CO2_ L2 - https://doi.org/10.1021/ja3045053 DB - PRIME DP - Unbound Medicine ER -