Synlett 2013; 24(17): 2327-2328
DOI: 10.1055/s-0033-1339856
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© Georg Thieme Verlag Stuttgart · New York

N,N,N,N′-Tetramethylethane-1,2-diamine (TMEDA)

Bharat Kumar Allam
Department of Chemistry (Centre of Advanced Study), Faculty of Science, Banaras Hindu University, Varanasi–221005, India   Email: allambharatkumar@gmail.com
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Further Information

Publication History

Publication Date:
05 September 2013 (online)

Dedicated to my parents and my esteemed supervisor Professor Dr. Krishna Nand Singh

Introduction

N,N,N,N′-Tetramethylethane-1,2-diamine (TMEDA) is a colorless, liquid, organic base with a fishy odor. TMEDA serves as an excellent donor of methylene and formyl groups under base switching.[1] It functions as an important ligand and additive for a broad spectrum of transition-metal-catalyzed reactions because of its unique ability to enhance the rate of metalation for a variety of compounds.[2] Because of its easy solvating and bidentate ligand properties it stabilizes and activates a number of organometallic reagents and metal salts. TMEDA exhibits a special affinity towards lithium ions and this feature allows BuLi/TMEDA to metalate many substrates.[3]