One-Step Trimethylstannylation of Benzyl and Alkyl Halides
View Author Information
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States
Energy Sciences Institute, Yale University, West Haven, Connecticut 06516, United States
*E-mail: [email protected]
*E-mail: [email protected]
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.
Cited By
This article is cited by 3 publications.
- Songyi Li, Chang Lian, Guanglu Yue, Jianning Zhang, Di Qiu, Fanyang Mo. Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes. The Journal of Organic Chemistry 2022, 87 (6) , 4291-4297. https://doi.org/10.1021/acs.joc.1c03135
- Silvia Roscales, Aurelio G. Csákÿ. Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid. ACS Omega 2019, 4 (9) , 13943-13953. https://doi.org/10.1021/acsomega.9b01608
- Jianpeng Ma, Yalin Li, Pengjun Wu, Jinhua Zhao, Weixin Zheng. Ultrasound‐Mediated Monodesulfonation of Polyphenol Sulfonate and One‐Pot Generation of Alkyl Aryl Ether under Solvent‐Free Conditions. ChemistrySelect 2023, 8 (17) https://doi.org/10.1002/slct.202300659