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Relevant academic research and scientific papers

Highly regioselective hydroiodination of terminal alkynes and silylalkynes with iodine and phosphorus reagents leading to internal iodoalkenes

Markovnikov-type hydroiodination of terminal alkynes with iodine and Ph2P(O)H took place selectively to afford the corresponding internal iodoalkenes in good yields. Combination of (PhO)2P(O)H and Ph 2P(O)OH instead of Ph2P(O)H also provided internal iodoalkenes in excellent yields. This hydroiodination is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups. In addition, direct synthesis of internal iodoalkenes from silylalkynes was also achieved by using a mixed system of iodine and phosphorus reagents.

Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2

By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides.

A convenient hydroiodination of alkynes using I2/PPh3/H2O and its application to the one-pot synthesis of trisubstituted alkenes via iodoalkenes using Pd-catalyzed cross-coupling reactions

A facile hydroiodination of alkynes using readily-available reagents such as I2, PPh3, and H2O has been developed. This is extended to the one-pot synthesis of trisubstituted alkenes from alkynes via iodoalkenes using Pd-c

Highly selective hydroiodation of alkynes using an iodine-hydrophosphine binary system

Figure presented A novel hydroiodation of alkynes (1) using an iodine/hydrophosphine binary system takes place regioselectively to provide the corresponding Markovnikov-type adducts (2) in good yield. This hydroiodation is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups.

A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans. The Royal Society of Chemistry 2010.