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The Ullmann Coupling Reaction:  A New Approach to Tetraarylstannanes
Journal article   Peer reviewed

The Ullmann Coupling Reaction:  A New Approach to Tetraarylstannanes

Nadim S Shaikh, Sean Parkin and Hans-Joachim Lehmler
Organometallics, Vol.25(17), pp.4207-4214
08/14/2006
DOI: 10.1021/om060456a

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Abstract

Several iodobenzenes form tetraarylstannanes, in addition to other products, under reaction conditions typically employed for the Ullmann reaction, i.e., activated copper bronze (a copper−tin alloy) and 7 days at 230 °C. The isolated yields of the tetraarylstannanes were low to good (8−58%). Significantly higher yields (54−64%) of tetraphenylstannane were obtained by the direct reaction of iodobenzene with an excess of tin powder (iodobenzene:tin = 1:1 w/w) under the same conditions. Crystal structure analysis reveals that tetrakis(4-carbomethoxyphenyl)stannane crystallizes in a tetragonal space group and has 4̄ symmetry, which is the case for many symmetrical tetraarylstannanes. However, tetrakis(2,4-dichlorophenyl)stannane, tetrakis(3,4-dichlorophenyl)stannane, and tetrakis(2,4-dimethylphenyl)stannane do not crystallize in a tetragonal space group and do not have real 4̄ symmetry.

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