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Metal‐Free Iodosulfonylation of Internal Alkynes: Stereodefined Access to Tetrasubstituted Olefins
Author(s) -
Kumar Ravi,
Dwivedi Vikas,
Sridhar Reddy Maddi
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700576
Subject(s) - chemistry , amide , heteroatom , stereoselectivity , yield (engineering) , sulfone , aldehyde , alkyne , organic chemistry , combinatorial chemistry , catalysis , alkyl , materials science , metallurgy
The stereoselective E ‐iodosulfonylation of internal alkynes for synthesizing highly defined tetrasubstituted olefins using sodium phenyl sulfinate and iodine has been achieved. Most of the alkynes explored are non‐symmetrical and the regioselection is under full control. Arylalkynes with various electron‐withdrawing groups like keto, aldehyde, ester, amide, cyano, sulfone, bromo, chloro and iodo on the other end are identified as successful precursors to yield the highly functionalized olefins. Alkynes directly tethered with heteroatoms are also found to be suitable substrates.