Cleavage of Si–Ar bond vs Si–Me bond: a remarkable counterion effect on reactivity

SK Tipparaju, SK Mandal, S Sur, VG Puranik…

Index: Tipparaju, Suresh Kumar; Mandal, Sunil K.; Sur, Surojit; Puranik, Vedavati G.; Sarkar, Amitabha Chemical Communications, 2002 , # 17 p. 1924 - 1925

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Abstract

We have previously described 1 that nucleophile-assisted Ar–Si bond cleavage is particularly facile when the arene ring is complexed with a Cr(CO) 3 fragment (Chart 1). Stability of the aryl anion intermediate anchored on Cr(CO) 3 moiety is believed to facilitate such desilylation. This reaction provides a very useful method for introducing electron-withdrawing substituents on the arene ring by an ipso substitution of the SiMe 3 group. The facility of Si–Ar bond cleavage ...