Details
| Original language | English |
|---|---|
| Pages (from-to) | 11-16 |
| Number of pages | 6 |
| Journal | Journal of Flow Chemistry |
| Volume | 3 |
| Issue number | 1 |
| Publication status | Published - 26 Mar 2013 |
Abstract
The coupling of tosylhydrazones derived from aldehydes or ketones with aryl boronic acids to yield the corresponding arylation products that was first developed in the group of Barluenga was achieved in a two-step flow protocol. Starting from the respective carbonyl compounds, tosylhydrazones were formed in the first flow step. These were directly transferred into the second reactor to be coupled with boronic acids. Remarkably, carbenes are postulated to be the highly reactive intermediates of this reaction. Both steps required heating which was managed by electromagnetic induction of a fixed bed material based on steel beads. A continuously conducted two-step flow processes over a period of almost 2 days gave the arylation product in 84% yield.
Keywords
- Barluenga reaction, boronic acids, flow reactor, hydrazones, inductive heating
ASJC Scopus subject areas
- Chemistry(all)
- Chemistry (miscellaneous)
- Chemical Engineering(all)
- Fluid Flow and Transfer Processes
- Chemistry(all)
- Organic Chemistry
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In: Journal of Flow Chemistry, Vol. 3, No. 1, 26.03.2013, p. 11-16.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Two-step flow synthesis of biarylmethanes by reductive arylation of tosylhydrazones
AU - Kupracz, Lukas
AU - Kirschning, Andreas
PY - 2013/3/26
Y1 - 2013/3/26
N2 - The coupling of tosylhydrazones derived from aldehydes or ketones with aryl boronic acids to yield the corresponding arylation products that was first developed in the group of Barluenga was achieved in a two-step flow protocol. Starting from the respective carbonyl compounds, tosylhydrazones were formed in the first flow step. These were directly transferred into the second reactor to be coupled with boronic acids. Remarkably, carbenes are postulated to be the highly reactive intermediates of this reaction. Both steps required heating which was managed by electromagnetic induction of a fixed bed material based on steel beads. A continuously conducted two-step flow processes over a period of almost 2 days gave the arylation product in 84% yield.
AB - The coupling of tosylhydrazones derived from aldehydes or ketones with aryl boronic acids to yield the corresponding arylation products that was first developed in the group of Barluenga was achieved in a two-step flow protocol. Starting from the respective carbonyl compounds, tosylhydrazones were formed in the first flow step. These were directly transferred into the second reactor to be coupled with boronic acids. Remarkably, carbenes are postulated to be the highly reactive intermediates of this reaction. Both steps required heating which was managed by electromagnetic induction of a fixed bed material based on steel beads. A continuously conducted two-step flow processes over a period of almost 2 days gave the arylation product in 84% yield.
KW - Barluenga reaction
KW - boronic acids
KW - flow reactor
KW - hydrazones
KW - inductive heating
UR - http://www.scopus.com/inward/record.url?scp=84883393743&partnerID=8YFLogxK
U2 - 10.1556/JFC-D-12-00021
DO - 10.1556/JFC-D-12-00021
M3 - Article
AN - SCOPUS:84883393743
VL - 3
SP - 11
EP - 16
JO - Journal of Flow Chemistry
JF - Journal of Flow Chemistry
SN - 2062-249X
IS - 1
ER -