Combination of NH2OH center dot HCl and NaIO4: an effective reagent for molecular iodine-free regioselective 1,2-difunctionalization of olefins and easy access of terminal acetals / Chakraborty Nirnita,Santra Sougata,Kundu Shrishnu Kumar,Hajra Alakananda,Zyryanov Grigory V.,Majee Adinath // RSC ADVANCES. - 2015. - V. 5, l. 70. - P. 56780-56788.

ISSN/EISSN:

2046-2069 / нет данных

Type:

Article

Abstract:

We have demonstrated a new application of our oxidizing reagent, a combination of NH2OH center dot HCl and NaIO4, 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.

Author keywords:

ELECTRON-WITHDRAWING SUBSTITUENTS; HYDROGEN-PEROXIDE; ORGANIC-SYNTHESIS; PALLADIUM(II)-CATALYZED ACETALIZATION; OXYGENATED NUCLEOPHILES; ALKENES; IODOHYDRINS; EPOXIDATION; OXIDATION; EPOXIDES

DOI:

10.1039/c5ra11092k

Web of Science ID:

ISI:000357805100038

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	ELECTRON-WITHDRAWING SUBSTITUENTS; HYDROGEN-PEROXIDE; ORGANIC-SYNTHESIS; PALLADIUM(II)-CATALYZED ACETALIZATION; OXYGENATED NUCLEOPHILES; ALKENES; IODOHYDRINS; EPOXIDATION; OXIDATION; EPOXIDES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	adinath.majee@visva-bharati.ac.in
Funding-Acknowledgement	BRNS, Govt. of India {[}37(2)/14/35/2014-BRNS/563]; CSIR, New Delhi, India {[}02(0168)/13/EMR-II]; Russian Scientific Fund {[}15-13-10033]
Funding-Text	A. Majee is pleased to acknowledge the financial support from BRNS, Govt. of India (Grant No. 37(2)/14/35/2014-BRNS/563). A. Hajra acknowledges CSIR, New Delhi, India (Grant No. 02(0168)/13/EMR-II) for financial support. We are thankful to DST-FIST and UGC-SAP. S. Santra and G. V. Zyryanov acknowledge the Russian Scientific Fund (Grant \# 15-13-10033) for funding.
Number-of-Cited-References	69
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	5
Journal-ISO	RSC Adv.
Doc-Delivery-Number	CM6NI