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Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal.
Org Lett. 2013 Sep 20; 15(18):4754-7.OL

Abstract

The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen S
School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Changzhou University , Changzhou 213164, P. R. China, and College of Chemistry & Engineering, Wenzhou University , Wenzhou, 325000, P. R. China.
Yu J
No affiliation info available
Jiang Y
No affiliation info available
Chen F
No affiliation info available
Cheng J
No affiliation info available

MeSH

AldehydesAlkynesBenzaldehydesCatalysisCyclizationIndansKetonesMolecular StructureRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24011165

Citation

Chen, Shuyou, et al. "Rhodium-catalyzed Direct Annulation of Aldehydes With Alkynes Leading to Indenones: Proceeding Through in Situ Directing Group Formation and Removal." Organic Letters, vol. 15, no. 18, 2013, pp. 4754-7.
Chen S, Yu J, Jiang Y, et al. Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal. Org Lett. 2013;15(18):4754-7.
Chen, S., Yu, J., Jiang, Y., Chen, F., & Cheng, J. (2013). Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal. Organic Letters, 15(18), 4754-7. https://doi.org/10.1021/ol4021145
Chen S, et al. Rhodium-catalyzed Direct Annulation of Aldehydes With Alkynes Leading to Indenones: Proceeding Through in Situ Directing Group Formation and Removal. Org Lett. 2013 Sep 20;15(18):4754-7. PubMed PMID: 24011165.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal. AU - Chen,Shuyou, AU - Yu,Jintao, AU - Jiang,Yan, AU - Chen,Fan, AU - Cheng,Jiang, Y1 - 2013/09/06/ PY - 2013/9/10/entrez PY - 2013/9/10/pubmed PY - 2014/3/1/medline SP - 4754 EP - 7 JF - Organic letters JO - Org Lett VL - 15 IS - 18 N2 - The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24011165/Rhodium_catalyzed_direct_annulation_of_aldehydes_with_alkynes_leading_to_indenones:_proceeding_through_in_situ_directing_group_formation_and_removal_ DB - PRIME DP - Unbound Medicine ER -