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. 2014 Jul 18;16(14):3656-9.
doi: 10.1021/ol501404x. Epub 2014 Jul 2.

Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives

Bo Jiang  1 , Xing-Jun Tu, Xue Wang, Shu-Jiang Tu, Guigen Li
Affiliations

Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives

Bo Jiang et al. Org Lett. .

Abstract

Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C-N, C-S, and C-C bonds, allowing direct formation of highly functionalized thiophenes with a wide diversity in substituents in a one-pot manner. A plausible mechanism for the domino process is proposed.

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Figures

Figure 1
Figure 1
Synthesis of O,N-heterocycles from N-sulfonyl azides with terminal alkynes.
Scheme 1
Scheme 1. Synthesis of Functionalized Thiophenes
Scheme 2
Scheme 2. Synthesis of Compounds 3
Figure 2
Figure 2
ORTEP drawing of 3a.
Scheme 3
Scheme 3. Domino Synthesis of Functionalized Thiophenes 6
Isolated yield.
Scheme 4
Scheme 4. Scope of Multicomponent Reactions
Figure 3
Figure 3
ORTEP drawing of 6a.
Scheme 5
Scheme 5. Mechanism Hypothesis for Forming 6
See this image and copyright information in PMC

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