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Synthesis of C4-Substituted Indoles via a Catellani and C-N Bond Activation Strategy.
- Source :
-
Organic letters [Org Lett] 2020 Nov 06; Vol. 22 (21), pp. 8267-8271. Date of Electronic Publication: 2020 Oct 13. - Publication Year :
- 2020
-
Abstract
- This paper describes the case of a cross study between the C-N bond cleavage reaction field and the Catellani-Lautens reaction system. A series of highly functionalized C4-substituted indoles were synthesized using this strategy. By screening the alkyl groups of amines, the energy barrier of C-N bond cleavage reaction was reduced and the corresponding allenization products were avoided. Finally, the density functional theory calculation shows that the inert C-N bond activation reaction is not a concerted process; on the contrary, the coupling reaction first generates indole quaternary ammonium salt, and then C-N bond cleavage occurs via an S <subscript>N</subscript> 2 process.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 22
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 33048560
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c02897