Synlett 2007(12): 1972-1973  
DOI: 10.1055/s-2007-984873
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Tris(trimethylsilyl)silane (TTMSS)

Jean-François Brazeau*
Institut de recherches cliniques de Montréal (IRCM), 110 avenue des Pins Ouest, Montréal, QC, Canada, H2W 1R7
e-Mail: brazeajf@ircm.qc.ca;
Further Information

Publication History

Publication Date:
27 June 2007 (online)

Introduction

Tris(trimethylsilyl)silane (TTMSS) has been used in many transformations, especially in radical chain reactions. Chatgilialoglu et al. demonstrated that this reagent can be a valuable substitute for tin reagents commonly used in radical processes. [1] The Si-H bond dissociation ­energy in TTMSS of 79 kcal·mol-1 is very similar to the Sn-H bond dissociation energy of 74 kcal·mol-1 in Bu3SnH. [2] The ease of purification and the low toxicity of TTMSS make it an attractive alternative to tin as a ­reducing agent. Interestingly, there are also reports ­demonstrating that the behavior of TTMSS can be very different from that of tin hydrides. [3]

This reagent is commercially available as a colorless ­liquid. [4] It should be stored under nitrogen because it is sensitive towards oxygen. [5] Reactions such as functional reductions, [6] hydrosilylations, [7] intramolecular cyclizations, [8] intermolecular reactions, [9] and non-radical reactions [10] can be performed with TTMSS.