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Triethylsiloxymethyl‐ N , N ‐dimethylamine, Et 3 SiOCH 2 NMe 2 : A Dimethylaminomethylation (Mannich) Reagent for O–H, S–H, P–H and Aromatic C–H Systems
Author(s) -
Gonzalez Paulina E.,
Sharma Hemant K.,
Chakrabarty Sanchita,
MettaMagaña Alejandro,
Pannell Keith H.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700902
Subject(s) - chemistry , dimethylamine , reagent , yield (engineering) , medicinal chemistry , electrophile , derivative (finance) , electrophilic aromatic substitution , organic chemistry , ring (chemistry) , materials science , economics , financial economics , metallurgy , catalysis
Triethylsiloxymethylamine, Et 3 SiOCH 2 NMe 2 , readily synthesized in high yield by the hydrosilylation reaction between Et 3 SiH and DMF, is an excellent ( N , N ‐dimethylamino)methyl transfer agent to a representative range of aliphatic alcohols, thiols, and Ph 2 PH (E–H) materials. The reactions are almost instantaneous at room temperature in inert solvents and require no activating agents to produce E–CH 2 NMe 2 products in high yields and illustrate the title compound as an excellent addition to the family of organic reagents. For aromatic alcohols, electrophilic substitution of the aromatic ring occurs in high yield. Crystal structures of new materials such as the cholestero–CH 2 NMe 2 derivative, 2–4‐[bis( N , N ‐dimethylamino)methyl]‐1‐naphthol, and the phosphine oxide derived from Ph 2 PCH 2 NMe 2 are reported.