RESEARCH ARTICLE · Organometallics · 2006

Reactions of M(N-2,6-i-Pr2C6H3)(CHR)(CH2R‘)2 (M = Mo, W) Complexes with Alcohols To Give Olefin Metathesis Catalysts of the Type M(N-2,6-i-Pr2C6H3)(CHR)(CH2R‘)(OR‘ ‘)

Amritanshu Sinha, Lourdes Pia H. Lopez, Richard R. Schrock, Adam S. Hock, Péter Müller

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Abstract

The reaction between M(NAr)(CH-t-Bu)(CH 2 -t-Bu) 2 (M = Mo, W, Ar = 2,6-i-Pr 2 C 6 H 3 ) and various alcohols (1-adamantyl-OH, t-BuOH, ArOH, (CF 3 ) 2 CHOH, (CF 3 ) 2 MeCOH, CF 3 Me 2 COH, (CF 3 ) 3 COH, C 6 F 5 OH) in pentane or toluene yields either complexes of the type M(NAr)(CH-t-Bu)(CH 2 -t-Bu)(OR), through direct addition of ROH across a Mo−C bond, or complexes of the type M(NAr)(CH 2 -t-Bu) 3 (OR), through direct addition of ROH across a Mo C bond. The trineopentyl species appear to be formed when the alcohol has a relatively low p K a value. The outcome also can depend on whether the alcohol is employed neat or in benzene, and mixtures are observed in some circumstances. The conversion of M(NAr)(CH 2 -t-Bu) 3 (OR) into M(NAr)(CH-t-Bu)(CH 2 -t-Bu)(OR) was shown to be unimolecular in several examples. Preliminary experiments have shown that M(NAr)(CH-t-Bu)(CH 2 -t-Bu)(OR) complexes are surprisingly active catalysts for various metathesis reactions, although conversion is sometimes limited by decomposition of intermediate alkylidenes to yield dimeric species that contain M M bonds. In contrast, M(NAr)(CH-t-Bu)(CH 2 -t-Bu) 2 species are virtually inactive for metathesis. X-ray structures are reported for Mo(NAr)(CH 2 -t-Bu) 3 (OC 6 F 5 ), Mo(NAr)(CH-t-Bu)(CH 2 -t-Bu)[OSi(O-t-Bu) 3 ], [Mo(NAr)(CH-t-Bu)(CH 2 -t-Bu)(OC 6 F 5 )] 2, and Mo(NAr)(CH-t-Bu)(CH 2 -t-Bu)(OC 6 F 5 )(PMe 3 ).

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