An Approach Towards Functional Dendrimers Based on the Hydroboration Reaction and Spontaneous Boron-Nitrogen Bond Formation
The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl (2) leads to the corresponding 2,2′‐bipyridylboronium cations 5 and 7 in almost quantitative yield. Using the monocation [(MeC6H4)B(Br){4,4′‐bis(but‐3′′‐enyl)...
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| Published in | European Journal of Inorganic Chemistry Vol. 2005; no. 21; pp. 4309 - 4316 |
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| Main Authors | , , , |
| Format | Book Review Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.11.2005
WILEY‐VCH Verlag Wiley |
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| Abstract | The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl (2) leads to the corresponding 2,2′‐bipyridylboronium cations 5 and 7 in almost quantitative yield. Using the monocation [(MeC6H4)B(Br){4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl}]+ (3Br) as a model system, it is shown that the olefinic side‐chains of such compounds are readily transformed into alkyldibromoborane functionalities by hydroboration with HBBr2. Subsequent addition of 4,4′‐dimethyl‐2,2′‐bipyridyl leads to the formation of a branched system of three 2,2′‐bipyridylboronium cations (9Br). The species 5 and 7 can be regarded as generation zero (G0) 2,2′‐bipyridylboronium dendrimers, and the hydroboration/B–N adduct formation sequence offers a convenient route for the assembly of higher generations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) |
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| AbstractList | Abstract
The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes
4
and
6
, respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl (
2
) leads to the corresponding 2,2′‐bipyridylboronium cations
5
and
7
in almost quantitative yield. Using the monocation [(MeC
6
H
4
)B(Br){4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl}]
+
(
3Br
) as a model system, it is shown that the olefinic side‐chains of such compounds are readily transformed into alkyldibromoborane functionalities by hydroboration with HBBr
2
. Subsequent addition of 4,4′‐dimethyl‐2,2′‐bipyridyl leads to the formation of a branched system of three 2,2′‐bipyridylboronium cations (
9Br
). The species
5
and
7
can be regarded as generation zero (G
0
) 2,2′‐bipyridylboronium dendrimers, and the hydroboration/B–N adduct formation sequence offers a convenient route for the assembly of higher generations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl (2) leads to the corresponding 2,2′‐bipyridylboronium cations 5 and 7 in almost quantitative yield. Using the monocation [(MeC6H4)B(Br){4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl}]+ (3Br) as a model system, it is shown that the olefinic side‐chains of such compounds are readily transformed into alkyldibromoborane functionalities by hydroboration with HBBr2. Subsequent addition of 4,4′‐dimethyl‐2,2′‐bipyridyl leads to the formation of a branched system of three 2,2′‐bipyridylboronium cations (9Br). The species 5 and 7 can be regarded as generation zero (G0) 2,2′‐bipyridylboronium dendrimers, and the hydroboration/B–N adduct formation sequence offers a convenient route for the assembly of higher generations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) The reaction of 1,4-bis- or 1,3,5-tris (bromoboryl) benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4'-bis(but-3"-enyl)-2,2'-bipyridyl (2) leads to the corresponding 2,2'-bipyridylboronium cations 5 and 7 in almost quantitative yield. Using the monocation [(MeC6H4)B(Br){4,4'-bis(but-3"-enyl)-2,2'-bipyridyl}](+) (3Br) as a model system, it is shown that the olefinic side-chains of such compounds are readily transformed into alkyldibromoborane functionalities by hydroboration with HBBr2. Subsequent addition of 4,4'-dimethyl-2,2'-bipyridyl leads to the formation of a branched system of three 2,2'-bipyridylboronium cations (9Br). The species 5 and 7 can be regarded as generation zero (GO) 2,2'-bipyridylboronium dendrimers, and the hydroboration/B-N adduct formation sequence offers a convenient route for the assembly of higher generations. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheirn, Germany, 2005). |
| Author | Haberecht, Monika C. Bolte, Michael Lerner, Hans-Wolfram Wagner, Matthias |
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| Keywords | boranes ELECTRONIC COMMUNICATION N ligands REDOX SYSTEMS dendrimers hydroboration LIGANDS COMPLEXES METALLODENDRIMERS CHARGE-TRANSFER 2,2'-BIPYRIDYLBORONIUM SALTS |
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| Snippet | The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl (2) leads to the... The reaction of 1,4-bis- or 1,3,5-tris (bromoboryl) benzenes 4 and 6, respectively, with 2 or 3 equiv. of 4,4'-bis(but-3"-enyl)-2,2'-bipyridyl (2) leads to the... Abstract The reaction of 1,4‐bis‐ or 1,3,5‐tris(bromoboryl)benzenes 4 and 6 , respectively, with 2 or 3 equiv. of 4,4′‐bis(but‐3′′‐enyl)‐2,2′‐bipyridyl ( 2 )... |
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| SubjectTerms | Boranes Chemistry Chemistry, Inorganic & Nuclear Dendrimers Hydroboration N ligands Physical Sciences Science & Technology |
| Title | An Approach Towards Functional Dendrimers Based on the Hydroboration Reaction and Spontaneous Boron-Nitrogen Bond Formation |
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