Triethylsiloxymethyl-N,N-dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O-H, S-H, P-H and Aromatic C-H Systems
Triethylsiloxymethyl-N,N-dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O-H, S-H, P-H and Aromatic C-H Systems
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DOI：
10.1002/ejoc.201700902
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发表时间：
2017-10-10
影响因子：
2.8
通讯作者：
Pannell, Keith H.
中科院分区：
文献类型：
--
作者：
Gonzalez, Paulina E.;Sharma, Hemant K.;Pannell, Keith H.
通过Et 3SiH和DMF之间的氢化硅烷化反应容易地以高产率合成的三乙基三甲基甲胺Et 3SiOCH 2NMe 2是脂肪醇、硫醇和Ph 2 PH（E-H）材料的代表性范围的优异的（N，N-二甲基氨基）甲基转移剂。该反应在室温下在惰性溶剂中几乎是瞬时的，并且不需要活化剂以高产率产生E-CH 2NMe 2产物，并且说明标题化合物是有机试剂家族的优异添加物。对于芳族醇，芳环的亲电取代以高产率发生。报道了胆固醇-CH_2NMe_2衍生物、2-[4-双（N，N-二甲氨基）甲基]-1-萘酚和Ph_2PCH_2NMe_2衍生的氧化膦等新材料的晶体结构。
Triethylsiloxymethylamine, Et3SiOCH2NMe2, readily synthesized in high yield by the hydrosilylation reaction between Et3SiH and DMF, is an excellent (N,N-dimethylamino) methyl transfer agent to a representative range of aliphatic alcohols, thiols, and Ph2PH (E-H) materials. The reactions are almost instantaneous at room temperature in inert solvents and require no activating agents to produce E-CH2NMe2 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-CH2NMe2 derivative, 2-4-[bis(N,N-dimethylamino)methyl]-1-naphthol, and the phosphine oxide derived from Ph2PCH2NMe2 are reported.