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  • Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols.

Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols.

Chemical communications (Cambridge, England) (2012-04-25)
Chuan Dai, Xiaofei Sun, Xingzhao Tu, Li Wu, Dan Zhan, Qingle Zeng
ABSTRACT

A ligand-free CuI-catalyzed cascade C-S and C-N cross coupling of (hetero)aryl ortho-dihalides and ortho-aminobenzenethiols has been developed, and various phenothiazines were synthesized with excellent regioselectivity. A possible mechanism is proposed for the cascade coupling.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium thiophenolate, technical grade, 90%
Sigma-Aldrich
Copper(I) iodide, 99.999% trace metals basis
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%
Supelco
Thiophenol, analytical standard
Sigma-Aldrich
Thiophenol, ≥99%
Sigma-Aldrich
Thiophenol, 97%
Sigma-Aldrich
Copper(I) iodide, 98%