Triethylsiloxymethyl‐N,N‐dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O–H, S–H, P–H and Aromatic C–H Systems
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 in...
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Published in | European journal of organic chemistry Vol. 2017; no. 37; pp. 5610 - 5616 |
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Main Authors | , , , , |
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Language | English |
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Abstract | 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.
Triethylsiloxymethyl‐N,N‐dimethylamine, Et3SiOCH2NMe2, prepared in high yield by Mo(CO)6‐catalyzed hydrosilylation of DMF, is an excellent CH2NMe2 transfer agent to OH, SH, and Caromatic–H‐bonded systems, with concomitant formation of Et3SiOH. The transfers occur rapidly under mild conditions, with high recovered yields, and require no activating agents. |
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AbstractList | 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.
Triethylsiloxymethyl‐N,N‐dimethylamine, Et3SiOCH2NMe2, prepared in high yield by Mo(CO)6‐catalyzed hydrosilylation of DMF, is an excellent CH2NMe2 transfer agent to OH, SH, and Caromatic–H‐bonded systems, with concomitant formation of Et3SiOH. The transfers occur rapidly under mild conditions, with high recovered yields, and require no activating agents. 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. |
Author | Chakrabarty, Sanchita Gonzalez, Paulina E. Metta‐Magaña, Alejandro Pannell, Keith H. Sharma, Hemant K. |
Author_xml | – sequence: 1 givenname: Paulina E. surname: Gonzalez fullname: Gonzalez, Paulina E. organization: University of Texas at El Paso – sequence: 2 givenname: Hemant K. surname: Sharma fullname: Sharma, Hemant K. organization: University of Texas at El Paso – sequence: 3 givenname: Sanchita surname: Chakrabarty fullname: Chakrabarty, Sanchita organization: University of Texas at El Paso – sequence: 4 givenname: Alejandro surname: Metta‐Magaña fullname: Metta‐Magaña, Alejandro organization: University of Texas at El Paso – sequence: 5 givenname: Keith H. surname: Pannell fullname: Pannell, Keith H. email: kpannell@utep.edu organization: University of Texas at El Paso |
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Keywords | SELF-ENCAPSULATION QUINONE METHIDE COMPLEXES Imminium ions TERTIARY PHOSPHINE OXIDE Amination LIGANDS SECONDARY AMIDES AMINES Mannich reaction Siloxymethylamine Synthetic methods CATALYZED REDUCTION EFFICIENT |
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Snippet | Triethylsiloxymethylamine, Et3SiOCH2NMe2, readily synthesized in high yield by the hydrosilylation reaction between Et3SiH and DMF, is an excellent... |
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SubjectTerms | Alcohol Aliphatic alcohols Aliphatic compounds Amination Chemical synthesis Chemistry Chemistry, Organic Crystal structure Hydrosilylation Imminium ions Mannich reaction Naphthol Phosphine oxide Physical Sciences Reagents Science & Technology Siloxymethylamine Synthetic methods Thiols |
Title | 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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