Rapid, highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron‐deficient tin(IV)porphyrin

Abstract

In this paper, rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) in the presence of catalytic amounts of high-valent [Sn IV (TPP)(OTf) 2 ] is reported. This catalytic system catalyzes trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMS-ethers were obtained in high yields and short reaction times at room temperature. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.

Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL‐101

“…The proposed mechanisms for trimethylsilylation and tetrahydropyranylation of alcohols and phenols are shown in Scheme . A plausible mechanism for these reactions is that the protective agent (DHP or HMDS) is first activated by tin(IV) porphyrin to afford 1 .…”

Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium‐containing polyoxometalate

“…All products were identified by comparison of their physical and spectral data with those of authentic samples, [39] and yields refer to isolated products. GC analysis was performed on a Shimadzu GC-16A instrument with a flame-ionization detector using silicon DC-200 or carbowax 20-M columns.…”

Highly efficient chemical fixation of carbon dioxide catalyzed by high-valent tetraphenylporphyrinatotin(IV) triflate

“…In continuation of our works on the use of tetraphenylporphyrinatotin(IV) perchlorate [26,27], tetraphenylporphyrinatotin (IV) trifluoromethanesulfonate [28][29][30], and tetraphenylporphyrinatotin (IV) tetrafluoroborate [31][32][33] in organic transformations, in the present work, we report an efficient method for chemical fixation of carbon dioxide with epoxides catalyzed by electron-deficient [Sn IV (TPP)(OTf) 2 ] at ambient pressure and temperature (Scheme 1).…”