Iodine-mediated acyloxyselenenylation of alkenes

Iodine-mediated acyloxyselenenylation of alkenes In the presence of I , an acyloxyselenenylation of alkenes with diselenides and carboxylic acids is developed. This metal-free iodine-mediated acyloxyselenenylation proceeds efficiently under mild reaction conditions, affording a series of 2-acyloxy- 1-selenides with high regioselectivity and in moderate to good yields. Keywords Acyloxyselenenylation · Acetoxyselenenylation · Formyloxyselenylation · I Introduction 1978). Although there are a series of 2-acetoxy-1-selenides prepared by above methods, other 2-acyloxy-1-selenides, 2-Acetoxy-1-selenides are important organoselenium com- especially 2-formyloxy-1-selenides are less. Therefore, the pounds; they can be prepared by acetoxyselenenylation of development of simple and general methods for the prepara- alkenes with selenenylating reagents in acetic acid, and after tion of 2-acyloxy-1-selenides and research on their unknown that an organylseleno group and an acetoxy are installed into chemical and biological properties is highly desired. the carbon–carbon double bond (Back 1987; Tiecco et al. Recently, we developed novel acetoxyselenenylation of 1990; Wirth 2000). In the electrophilic addition, the usually alkenes using inorganic haloid salts as catalysts (Shi et al. used selenenylating reagents PhSeX (X = Br, Cl) are com- 2015a, b). However, this procedure was not suitable for the mercially available (Paulmier 1986). However, the presence preparation of 2-formyloxy-1-selenides when using formic of toxic and moisture-sensitive nature of PhSeX, and the acid http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Papers Springer Journals

Iodine-mediated acyloxyselenenylation of alkenes

Loading next page...
 
/lp/springer_journal/iodine-mediated-acyloxyselenenylation-of-alkenes-ClgTWVVhYw
Publisher
Springer International Publishing
Copyright
Copyright © 2018 by Institute of Chemistry, Slovak Academy of Sciences
Subject
Chemistry; Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering; Biochemistry, general; Medicinal Chemistry; Materials Science, general; Biotechnology
ISSN
0366-6352
eISSN
1336-9075
D.O.I.
10.1007/s11696-018-0496-5
Publisher site
See Article on Publisher Site

Abstract

In the presence of I , an acyloxyselenenylation of alkenes with diselenides and carboxylic acids is developed. This metal-free iodine-mediated acyloxyselenenylation proceeds efficiently under mild reaction conditions, affording a series of 2-acyloxy- 1-selenides with high regioselectivity and in moderate to good yields. Keywords Acyloxyselenenylation · Acetoxyselenenylation · Formyloxyselenylation · I Introduction 1978). Although there are a series of 2-acetoxy-1-selenides prepared by above methods, other 2-acyloxy-1-selenides, 2-Acetoxy-1-selenides are important organoselenium com- especially 2-formyloxy-1-selenides are less. Therefore, the pounds; they can be prepared by acetoxyselenenylation of development of simple and general methods for the prepara- alkenes with selenenylating reagents in acetic acid, and after tion of 2-acyloxy-1-selenides and research on their unknown that an organylseleno group and an acetoxy are installed into chemical and biological properties is highly desired. the carbon–carbon double bond (Back 1987; Tiecco et al. Recently, we developed novel acetoxyselenenylation of 1990; Wirth 2000). In the electrophilic addition, the usually alkenes using inorganic haloid salts as catalysts (Shi et al. used selenenylating reagents PhSeX (X = Br, Cl) are com- 2015a, b). However, this procedure was not suitable for the mercially available (Paulmier 1986). However, the presence preparation of 2-formyloxy-1-selenides when using formic of toxic and moisture-sensitive nature of PhSeX, and the acid

Journal

Chemical PapersSpringer Journals

Published: May 28, 2018

References

You’re reading a free preview. Subscribe to read the entire article.


DeepDyve is your
personal research library

It’s your single place to instantly
discover and read the research
that matters to you.

Enjoy affordable access to
over 18 million articles from more than
15,000 peer-reviewed journals.

All for just $49/month

Explore the DeepDyve Library

Search

Query the DeepDyve database, plus search all of PubMed and Google Scholar seamlessly

Organize

Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place.

Access

Get unlimited, online access to over 18 million full-text articles from more than 15,000 scientific journals.

Your journals are on DeepDyve

Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.

All the latest content is available, no embargo periods.

See the journals in your area

DeepDyve

Freelancer

DeepDyve

Pro

Price

FREE

$49/month
$360/year

Save searches from
Google Scholar,
PubMed

Create lists to
organize your research

Export lists, citations

Read DeepDyve articles

Abstract access only

Unlimited access to over
18 million full-text articles

Print

20 pages / month

PDF Discount

20% off