Abstract
Trialkylstannanes are good leaving groups that have been used for the formation of carbon-metal bonds to electrode surfaces for analyses of single-molecule conductivity. Here, we report the multistep synthesis of two amide-containing compounds that are of interest in studies of molecular rectifiers. Each molecule has two trimethylstannyl units, one linked by a methylene and the other by an ethylene group. To account for the very different reactivities of the parent halides, a new methodology for one-step trimethylstannylation was developed and optimized.
| Original language | English |
|---|---|
| Pages (from-to) | 9483-9488 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 81 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - Oct 7 2016 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
One-Step Trimethylstannylation of Benzyl and Alkyl Halides. / Jiang, Jianbing; Crabtree, Robert H.; Brudvig, Gary W.
In: Journal of Organic Chemistry, Vol. 81, No. 19, 07.10.2016, p. 9483-9488.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - One-Step Trimethylstannylation of Benzyl and Alkyl Halides
AU - Jiang, Jianbing
AU - Crabtree, Robert H.
AU - Brudvig, Gary W
PY - 2016/10/7
Y1 - 2016/10/7
N2 - Trialkylstannanes are good leaving groups that have been used for the formation of carbon-metal bonds to electrode surfaces for analyses of single-molecule conductivity. Here, we report the multistep synthesis of two amide-containing compounds that are of interest in studies of molecular rectifiers. Each molecule has two trimethylstannyl units, one linked by a methylene and the other by an ethylene group. To account for the very different reactivities of the parent halides, a new methodology for one-step trimethylstannylation was developed and optimized.
AB - Trialkylstannanes are good leaving groups that have been used for the formation of carbon-metal bonds to electrode surfaces for analyses of single-molecule conductivity. Here, we report the multistep synthesis of two amide-containing compounds that are of interest in studies of molecular rectifiers. Each molecule has two trimethylstannyl units, one linked by a methylene and the other by an ethylene group. To account for the very different reactivities of the parent halides, a new methodology for one-step trimethylstannylation was developed and optimized.
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UR - http://www.scopus.com/inward/citedby.url?scp=84990861456&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b01883
DO - 10.1021/acs.joc.6b01883
M3 - Article
VL - 81
SP - 9483
EP - 9488
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -