P(MeNCH2CH2)3N:  An Efficient Silylation Catalyst

and, Bosco A. D'Sa; Verkade, John G.

doi:10.1021/ja961010w

Cited by 60 publications

(13 citation statements)

References 31 publications

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“…153 Also, kinetic resolution of allylic alcohols by acylations catalyzed by 75 have been reported (Scheme 35 Compound 74 has also been used to catalyze the intramolecular aldol (Scheme 36) 155 and in catalytic preparations of isocyanurates 156 and silyl ethers. 157…”

Section: Reactions Catalyzed By Trialkylphosphinesmentioning

confidence: 99%

Alkyl Phosphines as Reagents and Catalysts in Organic Synthesis

Valentine¹,

Hillhouse²

2003

Synthesis

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A literature review of the major stoichiometric uses of tertiary phosphines, with particular emphasis on the relative abilities of trialkylphosphines and triarylphosphines in Wittig, Staudinger, or Mitsunobu reactions, is presented. Pronounced differences in reaction rates and selectivity, product yields and ease of by-product removal are often observed when trialkylphosphines are compared with triarylphosphines as promoters in these types of reactions. Also presented here is a compilation of some useful physical properties for selected trialkylphosphines, their usual methods of preparation and typical uses in organic synthesis. 4Reactions Catalyzed by Trialkylphosphines 5Michael Reaction 6Conclusions

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Section: Reactions Catalyzed By Trialkylphosphinesmentioning

confidence: 99%

Alkyl Phosphines as Reagents and Catalysts in Organic Synthesis

Valentine¹,

Hillhouse²

2003

Synthesis

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“…As it is widely known, silyl ethers are resistant to oxidation, have a good stability for most non-acidic reagents and are easily deprotected to provide the free alcohols [3]. Generally, the formation of silyl ethers carried out by treatment of parent alcohols with silyl halides or silyl triflates in the presence of stoichiometric amounts of a base [4][5][6], Li 2 S [7], and occasionally with a nonionic super base catalyst [8][9][10][11]. However, these base-catalyzed silylation methods have serious disadvantages, since careful extraction and filtration are required to remove ammonium salts derived from the reaction of by-produced acids and co-bases during the silylation reaction.…”

Section: Introductionmentioning

confidence: 99%

Sulfonated Ordered Nanoporous Carbon (CMK-5-SO3H) as an Efficient and Highly Recyclable Catalyst for the Silylation of Alcohols and Phenols with Hexamethyldisilazane (HMDS)

2011

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An environmentally friendly catalytic system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane can be successfully carried out for the first time over sulfonated mesoporous carbon catalyst (CMK-5-SO 3 H) in dichloromethane at ambient temperature and excellent conversions were obtained. Furthermore, the catalyst displays high activity and thermal stability (to 200°C) and it can be reused repeatedly for at least 25 cycles without any evidence of loss of activity, confirming the stability of covalent bonding of acidic centers.

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“…15b We previously reported reactions in which proazaphosphatranes can activate silicon functionalities, 17-23 as for example in the silylation of alcohols using tert-butyldimethylsilyl chloride, 17,18 the synthesis of cyanohydrins via the addition of a trialkylsilylcyanide to carbonyl compounds, 19,20 the desilylation of TBDMS ethers, 21 and the nucleophilic aromatic substitution of aryl fluorides with aryl silylethers. 22,23 Because proazaphosphatranes can activate silicon functional groups [17][18][19][20][21][22][23] in addition to functioning as strong Lewis bases, 15,16 it occurred to us that in view of the paucity of reports in which the catalytic activation of TMS-dithiane for carbonyl umpolung 13,14 has been utilized, proazaphosphatranes might function well in such reactions. Here we report the use of a proazaphosphatrane as an efficient catalyst for 1,3-dithiane addition to the carbonyl of aldehydes as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%