Regio- and Stereoselective Allylindation of Alkynes Using InBr₃ and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes

Regioselective -allylindation of alkynes was achieved using InBr₃ and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The...

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Published inMolecules (Basel, Switzerland) Vol. 23; no. 8; p. 1884
Main Authors Nishimoto, Yoshihiro, Yi, Junyi, Takata, Tatsuaki, Baba, Akio, Yasuda, Makoto
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 27.07.2018
MDPI
Subjects
alkyne
Alkynes
allylic silane
allylmetalation
Aromatic compounds
Communication
Cross coupling
Indium
Investigations
Iodine
Silanes
Solvents
Spectral analysis
Stereoselectivity
indium
alkyne
allylmetalation
allylic silane
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Summary:Regioselective -allylindation of alkynes was achieved using InBr₃ and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I₂ to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23081884