Issue 20, 2023

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe3)2

Abstract

A chemo- and regioselective synthesis of 2-benzhydryl and 2,3-disubstituted indoles via cyclization and regiocontrolled Truce–Smiles (T–S) rearrangement is disclosed. A cascade 5-endo-dig cyclization of 2-amino diphenylacetylenes mediated by KN(SiMe3)2 is followed by a regiocontrolled T–S reaction. This system provides the first example of T–S regioselectivity and is controlled by ligands on K+.

Graphical abstract: A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe3)2

Supplementary files

Article information

Article type
Research Article
Submitted
17 Jul 2023
Accepted
05 Sep 2023
First published
18 Sep 2023

Org. Chem. Front., 2023,10, 5265-5273

Author version available

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe3)2

F. Zhou, H. Jin, Z. Xiang, P. J. Walsh and J. Li, Org. Chem. Front., 2023, 10, 5265 DOI: 10.1039/D3QO01105D

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