Synthesis of functionalized iodoalkenes using a multicomponent reaction triggered by electrophilic iodination of alkenyldiazoacetates. (Downloadable article, 2018) [WorldCat.org]
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Synthesis of functionalized iodoalkenes using a multicomponent reaction triggered by electrophilic iodination of alkenyldiazoacetates.

Author: Ryota Kajihara; Shingo Harada; Jun Ueda; Tetsuhiro Nemoto
Publisher: [Amsterdam] : Elsevier, 2018.
Edition/Format:   Downloadable article : Document   Computer File : English
Publication:Tetrahedron letters
Summary:
Graphical abstract: Highlights: A novel iodoalkoxylation of alkenyl diazoacetates has been developed. This metal-free iodination reaction proceeds without the use of a catalyst. The methodology efficiently provides trisubstituted iodoalkene derivatives. The obtained vinyl iodides were applied to Suzuki-Miyaura coupling reactions. Abstract: Diazo compounds are frequently used as precursors of metal carbenoids and act  Read more...
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Details

Material Type: Document, Internet resource
Document Type: Internet Resource, Article, Computer File
All Authors / Contributors: Ryota Kajihara; Shingo Harada; Jun Ueda; Tetsuhiro Nemoto
ISSN:0040-4039
OCLC Number: 1051898285
Notes: In: Tetrahedron letters, Vol. 59, no. 20 (2018), p.1906-1908.
Description: 1 online resource

Abstract:

Graphical abstract: Highlights: A novel iodoalkoxylation of alkenyl diazoacetates has been developed. This metal-free iodination reaction proceeds without the use of a catalyst. The methodology efficiently provides trisubstituted iodoalkene derivatives. The obtained vinyl iodides were applied to Suzuki-Miyaura coupling reactions. Abstract: Diazo compounds are frequently used as precursors of metal carbenoids and act as soft nucleophiles even without the use of metal catalysts. The resulting diazonium species may also be trapped by various nucleophiles. The introduction of an iodine functionality applicable for the coupling reaction into an alkenyl diazo compound, however, has not been reported. We developed iodoalkoxylation reactions of alkenyl diazoacetates using an electrophilic iodinating reagent and oxygen nucleophile. This catalyst-free multicomponent reaction proceeded regioselectively, furnishing trisubstituted vinyl iodides in 31%-71% yield. The synthesized iodoalkenes were converted into the corresponding olefins with various functionalities in good yield via Suzuki-Miyaura coupling reactions with arylboronic acids under palladium catalysis to demonstrate the synthetic utility of the developed reaction sequence.

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