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Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N ‐[(Trimethylsiloxy)methyl]phthalimide
Author(s) -
Asano Narumi,
Sasaki Keita,
Chataigner Isabelle,
Shigeno Masanori,
Kondo Yoshinori
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.201701440
Subject(s) - phthalimide , chemistry , halogen , formaldehyde , stoichiometry , sodium , polymer chemistry , organic chemistry , medicinal chemistry , alkyl
The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N ‐[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one‐step procedure. A variety of alkynylsilanes possessing electron‐donating, electron‐withdrawing, and halogen groups (including heteroaryl‐substituted alkynylsilanes) provide hydroxymethylated products.