Heck-Mizoroki coupling of vinyliodide and applications in the synthesis of dienes and trienes

Vinyliodide reacts chemoselectively under Heck-Mizoroki conditions with terminal alkenes, including vinylboronate esters, to give dienes. The resulting dienylboronates undergo Suzuki-Miyaura couplings with aryl, heteroaryl and alkenyl halides to access dienes and trienes.

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 51; no. 57; pp. 11409 - 11412
Main Authors Madden, Katrina S., David, Sylvain, Knowles, Jonathan P., Whiting, Andrew
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.07.2015
Subjects
Alkenes
Alkenes - chemical synthesis
Alkenes - chemistry
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Couplings
Dienes
Esters
Joining
Palladium - chemistry
Physical Sciences
Polyenes - chemical synthesis
Polyenes - chemistry
Science & Technology
Stereoisomerism
Synthesis
Terminals
Trienes
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
CHAIN
ACID
VINYLBORONATE ESTER
ARYL HALIDES
4,4,6-TRIMETHYL-2-VINYL-1,3,2-DIOXABORINANE
POLYENE NATURAL-PRODUCTS
STEREOSELECTIVE-SYNTHESIS
EFFICIENT
2-CARBON BUILDING-BLOCK
Online AccessGet full text

Cover

More Information
Summary:Vinyliodide reacts chemoselectively under Heck-Mizoroki conditions with terminal alkenes, including vinylboronate esters, to give dienes. The resulting dienylboronates undergo Suzuki-Miyaura couplings with aryl, heteroaryl and alkenyl halides to access dienes and trienes.
Bibliography:researchfish
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc03273c