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. 2020 Jul 17;22(14):5462-5465.
doi: 10.1021/acs.orglett.0c01834. Epub 2020 Jun 26.

Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene

Chiyu Wei  1 , Ying He  1 , Jin Wang  2 , Xiaohan Ye  1 , Lukasz Wojtas  1 , Xiaodong Shi  1
Affiliations

Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene

Chiyu Wei et al. Org Lett. .

Abstract

Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C-C unsaturated bonds is reported. Reactions of unactivated alkyne, alkene, and allene, respectively, with disulfides or diselenides in HFIP led to desired products in good to excellent yields (up to 96%). In contrast, other solvents, such as isopropanol and dichloroethane, could not promote the same reaction. This method revealed an example of HFIP-promoted transformations under the mild conditions, which greatly highlighted the unique reactivity of this special solvent.

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Conflict of interest statement

The authors claim no competing financial interest.

Figures

Figure 1.
Figure 1.
HFIP promoted internal alkyne diselenation
Figure 2.
Figure 2.
Disulfidation and diselenation reactions
Scheme 1.
Scheme 1.
HFIP promoted challenging transformations
Scheme 2.
Scheme 2.
HFIP Promoted Alkyne Diselenationa aReaction conditions: alkyne (0.4 mmol) and diselenide (0.2 mmol) were added into HFIP:HFA = 19:1 (1 mL), and the mixture was stirred at 60 °C for 24 h. Isolated yield. b3 days. cUnder room temperature. d12 h.
See this image and copyright information in PMC

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