A versatile synthesis of 9-BBN derivatives from organometallic reagents and 9-(triisopropylsilyl)thio-9-borabicyclo[3.3.1]nonane

Representative B-substituted-9-BBNs (3) are efficiently prepared from either organolithium or Grignard reagents through their addition to (TIPS)S-9-BBN (1) which is readily available from TIPSSH and 9-BBN-H. The thermally induced collapse of the intermediate ‘ate’ complexes (2) produces 3 which is easily isolated in good yield and high purity.