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Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols.
J Am Chem Soc. 2014 Jan 22; 136(3):834-7.JA

Abstract

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Seoane A
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
Casanova N
No affiliation info available
Quiñones N
No affiliation info available
Mascareñas JL
No affiliation info available
Gulías M
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24313353

Citation

Seoane, Andrés, et al. "Straightforward Assembly of Benzoxepines By Means of a rhodium(III)-catalyzed C-H Functionalization of O-vinylphenols." Journal of the American Chemical Society, vol. 136, no. 3, 2014, pp. 834-7.
Seoane A, Casanova N, Quiñones N, et al. Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols. J Am Chem Soc. 2014;136(3):834-7.
Seoane, A., Casanova, N., Quiñones, N., Mascareñas, J. L., & Gulías, M. (2014). Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols. Journal of the American Chemical Society, 136(3), 834-7. https://doi.org/10.1021/ja410538w
Seoane A, et al. Straightforward Assembly of Benzoxepines By Means of a rhodium(III)-catalyzed C-H Functionalization of O-vinylphenols. J Am Chem Soc. 2014 Jan 22;136(3):834-7. PubMed PMID: 24313353.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols. AU - Seoane,Andrés, AU - Casanova,Noelia, AU - Quiñones,Noelia, AU - Mascareñas,José L, AU - Gulías,Moisés, Y1 - 2013/12/12/ PY - 2013/12/10/entrez PY - 2013/12/10/pubmed PY - 2013/12/10/medline SP - 834 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 136 IS - 3 N2 - Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/24313353/Straightforward_assembly_of_benzoxepines_by_means_of_a_rhodium_III__catalyzed_C_H_functionalization_of_o_vinylphenols_ DB - PRIME DP - Unbound Medicine ER -