TY - JOUR
T1 - One-Step Trimethylstannylation of Benzyl and Alkyl Halides
AU - Jiang, Jianbing
AU - Crabtree, Robert H.
AU - Brudvig, Gary W.
N1 - Funding Information:
This work was supported by a grant from the U.S. Department of Energy (DE-FG02-07ER15909) and a generous grant from the TomKat Foundation. We would like to thank Terence Wu and Mousumi Ghosh of the Yale West Campus Analytical Core staff for help with instrumentation.
Publisher Copyright:
© 2016 American Chemical Society.
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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U2 - 10.1021/acs.joc.6b01883
DO - 10.1021/acs.joc.6b01883
M3 - Article
AN - SCOPUS:84990861456
VL - 81
SP - 9483
EP - 9488
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -