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

• Published in: European journal of organic chemistry Vol. 2017; no. 37; pp. 5610 - 5616
• Main Authors: Gonzalez, Paulina E., Sharma, Hemant K., Chakrabarty, Sanchita, Metta‐Magaña, Alejandro, Pannell, Keith H.
• Format: Journal Article
• Language: English
• Published: 10.10.2017
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201700902

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.