Alkynylboranes: A Practical Approach by Zinc-Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8-Naphthalenediaminatoborane

Under zinc Lewis acid catalysis, terminal alkynes coupled dehydrogenatively with 1,8‐naphthalenediaminatoborane [HB(dan)]. It is important to note that the resulting alkynylboranes with an C(sp)B(dan) bond are isolable by column chromatography on silica gel (SiO2) and are usable as coupling partner...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 357; no. 1; pp. 77 - 82
Main Authors Tsuchimoto, Teruhisa, Utsugi, Hirokazu, Sugiura, Tetsuya, Horio, Shin
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.01.2015
WILEY‐VCH Verlag
Wiley
Subjects
Alkynes
Bonding
boron
Catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Dehydrogenation
Joining
Lewis acids
multiple bonds
Physical Sciences
Science & Technology
Silica gel
Terminals
Zinc
ORGANOBORON COMPOUNDS
ROOM-TEMPERATURE
ARENES
Lewis acids
catalysis
ALKYLBORONIC ESTERS
FUNCTIONALIZATION
ARYL HALIDES
dehydrogenation
PINACOL
C-H BORYLATION
BORENIUM CATIONS
multiple bonds
boron
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Summary:Under zinc Lewis acid catalysis, terminal alkynes coupled dehydrogenatively with 1,8‐naphthalenediaminatoborane [HB(dan)]. It is important to note that the resulting alkynylboranes with an C(sp)B(dan) bond are isolable by column chromatography on silica gel (SiO2) and are usable as coupling partners for palladium‐ and copper‐catalyzed cross‐coupling reactions with (hetero)aryl halides.
Bibliography:ark:/67375/WNG-0RCBTBVZ-6
ArticleID:ADSC201400767
istex:585D0B3E4C58449D78A0B1D97511FF552EBDA6D4
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400767