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Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism
Author(s) -
Liu Bin,
AlegreRequena Juan V.,
Paton Robert S.,
Miyake Garret M.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904520
Subject(s) - scope (computer science) , mechanism (biology) , reactivity (psychology) , chemistry , reagent , combinatorial chemistry , biophysics , biochemical engineering , organic chemistry , computer science , medicine , philosophy , epistemology , biology , engineering , alternative medicine , pathology , programming language
1,2‐Dithio‐1‐alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2‐dithio‐1‐alkenes often demand transition metal catalysts, specialized or air‐sensitive ligands, high temperatures, and disulfides (R 2 S 2 ). Herein, a general and efficient strategy utilizing ethynylbenziodoxolone (EBX) reagents and thiols is presented that results in the formation of 1,2‐dithio‐1‐alkenes with excellent regioselectivity and stereoselectivity through unprecedented reactivity between the EBX and the thiol. This operationally simple procedure utilizes mild conditions, which result in a broad substrate scope and high functional‐group tolerance. The observed unexpected reactivity has been rationalized through both experimental results and DFT calculations.