Easy to Handle Silylating Reagent with High Reactivity

Due to their unique chemical reactivity and potential functional utility, organosilicon compounds are frequently searched in synthetic chemistry and material science. Therefore, synthesis of easy to handle organosilicon reagents with high reactivity is an attractive subject. Yorimitsu et al. recently reported the utility of 1,2-di-tert-butoxy-1,1,2,2-tetramethyldisilane (1), which is stable in the air and can be handled easily, as a useful silylating reagent and its unique and useful silylating reactions. For example, copper-catalyzed ring-opening silylation of benzofurans with 1 affords (E)-o-(β-silylvinyl)phenols with complete E/Z selectivity and high yields under mild conditions.¹⁾ In addition, the coupling reaction of a series of chloroarenes and 1 using SingaCycle™-A3 as a precatalyst results in the corresponding silylarenes in high yields.²⁾ These reactions indicate the potential application of 1 as a useful silylating reagent. 1 is expected to be used in more practical and unique organosilicon compounds and their synthesis methods in the future.

Related Products

D5736

1,2-Di-tert-butoxy-1,1,2,2-tetramethyldisilane

C2387

SingaCycle™-A3

B0060

2,3-Benzofuran

References

• 1) Copper-Catalyzed Ring-Opening Silylation of Benzofurans with Disilane
  • H. Saito, K. Nogi, H. Yorimitsu, Angew. Chem. Int. Ed. 2018, 57, 11030.
• 2) Palladium-Catalyzed Silylation of Aryl Chlorides with Bulky Dialkoxydisilanes
  • K. Fukui, H. Saito, J. Shimokawa, H. Yorimitsu, Synlett 2020, 31, 1328.