Beilstein J. Org. Chem.2019,15, 2747–2752, doi:10.3762/bjoc.15.265
of the α-iodo intermediate, and methodology studies demonstrate that alkyl-capped, asymmetric, internal alkynes undergo a regiospecifichydration, also via the 5-exo-dig NGP pathway.
Keywords: α-iodo intermediate; internal alkyne; iodine-mediated hydration; neighboring group participation
; regiospecifichydration; Findings
The Kucherov reaction is one of the most well-known approaches for the hydration of alkynes. This reaction, originally published in 1881, requires the use of mercury(II) salts in catalytic quantities [1][2]. Countless studies have shown that mercury-based compounds are
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Graphical Abstract
Scheme 1:
Proposed mechanism for the iodine-mediated hydration of terminal alkynes 1 [15].