Concepedia

Strong Counteranion Effects on the Catalytic Activity of Cationic Silicon Lewis Acids in Mukaiyama Aldol and Diels−Alder Reactions

Kenji Hara, Ryuto Akiyama, Masaya Sawamura

Organic Letters · 2005 · 113 citations · 14 references

DOI

Concepts

Abstract

[chemical reaction: see text]. A toluene-coordinated silyl borate, [Et3Si(toluene)]B(C6F5)4, demonstrated catalytic activities significantly higher than those of Me3SiOTf and Me3SiNTf2 in Mukaiyama aldol and Diels-Alder reactions.

References

14

Room-Temperature Catalytic Hydrodefluorination of C(sp<sup>3</sup>)−F Bonds

Valerie Scott, R. Celenligil-Cetin, Oleg V. Ozerov · Journal of the American Chemical Society · 2005 · 323 citations

, , +7

Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction

B. Mathieu, Léon Ghosez · Tetrahedron · 2002 · 144 citations

, , +14

N-Trimethylsilyl-bis(trifluoromethanesulfonyl)imide: a better carbonyl activator than trimethylsilyl triflate

B. Mathieu, Léon Ghosez · Tetrahedron Letters · 1997 · 123 citations

, , +4

Chemistry of organosilicon compounds. 292. An NMR study of the formation of silyloxonium ions by using tetrakis[3,5-bis(trifluoromethyl)phenyl]borate as counteranion

Mitsuo Kira, Takakazu Hino, Hideki Sakurai · Journal of the American Chemical Society · 1992 · 122 citations

, , +4

Tetrakis(pentafluorophenyl)borate: a new anion for silylium cations in the condensed phase

Joseph B. Lambert, Shizhong Zhang · Journal of the Chemical Society Chemical Communications · 1993 · 121 citations

, , +3