Combination of NH sub(2)OH.HCl and NaIO sub(4): an effective reagent for molecular iodine-free regioselective 1,2-difunctionalization of olefins and easy access of terminal acetals

We have demonstrated a new application of our oxidizing reagent, a combination of NH sub(2)OH.HCl and NaIO sub(4), in the first generalized regioselective 1,2-difunctionalization of olefins. It is a general method for the preparation of beta -iodo- beta '-hydroxy ethers, beta -iodo ethers, beta...

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Bibliographic Details
Published in:RSC advances 2015-06, Vol.5 (70), p.56780-56788
Main Authors: Chakraborty, Nirnita, Santra, Sougata, Kundu, Shrishnu Kumar, Hajra, Alakananda, Zyryanov, Grigory V, Majee, Adinath
Format: Article
Language:English
Subjects:
Acetals
Ethers
Media
Nucleophiles
Olefins
Oxidation
Synthesis (chemistry)
Terminals
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Summary:We have demonstrated a new application of our oxidizing reagent, a combination of NH sub(2)OH.HCl and NaIO sub(4), in the first generalized regioselective 1,2-difunctionalization of olefins. It is a general method for the preparation of beta -iodo- beta '-hydroxy ethers, beta -iodo ethers, beta -iodohydrin, and beta -iodo acetoxy compounds using different reaction media. The reactions are highly regioselective, always affording Markovnikov's type addition products. The methodology is also applicable for the easy access of terminal acetals. Molecular iodine-free synthesis, room temperature reaction conditions, high yields, use of less expensive reagents, mild reaction conditions, broad applicability of nucleophiles, and applicability for gram-scale synthesis are the notable advantages of this present protocol.
ISSN:2046-2069
DOI:10.1039/c5ra11092k