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.
Links
MeSH
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 -