Direct Synthesis of C4-Acyl Indoles via C–H Acylation

The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C–H acylation for the construction of C4-acyl indoles via a Catellani–Lauten...

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Published inOrganic letters Vol. 26; no. 23; pp. 4998 - 5003
Main Authors Zhang, Bo-Sheng, Zhang, Ze-Qiang, Guo, Tian-Jiao, Oliveira, João C. A., Warratz, Svenja, Deng, Bao-Jie, Wang, Yi-Ming, Zhou, Jun-Shi, Gou, Xue-Ya, Wang, Xi-Cun, Quan, Zheng-Jun, Ackermann, Lutz
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.06.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ROUTE
POTENT
REGIOSELECTIVE SYNTHESIS
ARYL IODIDES
BOND
CLEAVAGE
EFFICIENT
DERIVATIVES
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Abstract The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C–H acylation for the construction of C4-acyl indoles via a Catellani–Lautens cyclization strategy. In addition, we systematically studied the ortho C–H acylation mechanism of iodoaniline through density functional theory (DFT) calculations and combined experimental results to elucidate the principle of high chemoselectivity brought by triazine benzoate as an acylation reagent.
AbstractList The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C-H acylation for the construction of C4-acyl indoles via a Catellani-Lautens cyclization strategy. In addition, we systematically studied the ortho C-H acylation mechanism of iodoaniline through density functional theory (DFT) calculations and combined experimental results to elucidate the principle of high chemoselectivity brought by triazine benzoate as an acylation reagent.
The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C-H acylation for the construction of C4-acyl indoles via a Catellani-Lautens cyclization strategy. In addition, we systematically studied the C-H acylation mechanism of iodoaniline through density functional theory (DFT) calculations and combined experimental results to elucidate the principle of high chemoselectivity brought by triazine benzoate as an acylation reagent.
Author Oliveira, João C. A.
Warratz, Svenja
Guo, Tian-Jiao
Zhou, Jun-Shi
Quan, Zheng-Jun
Wang, Xi-Cun
Ackermann, Lutz
Zhang, Ze-Qiang
Deng, Bao-Jie
Wang, Yi-Ming
Zhang, Bo-Sheng
Gou, Xue-Ya
AuthorAffiliation Institut für Organische und Biomolekulare Chemie and Wöhler-Research Institute for Sustainable Chemistry (WISCh)
College of Chemistry and Chemical Engineering
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  surname: Quan
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Issue 23
Keywords FUNCTIONALIZATION
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REGIOSELECTIVE SYNTHESIS
ARYL IODIDES
BOND
CLEAVAGE
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DERIVATIVES
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Snippet The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported....
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Direct Synthesis of C4-Acyl Indoles via C–H Acylation
URI http://dx.doi.org/10.1021/acs.orglett.4c01658
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