Stereospecific Stille Cross-Couplings Using Mn(II)Cl2

Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp-and sp(2)-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn (II) Cl-2 complexes valone, or with assistance from copper, catalyze the stereospecific cross-coupling of alpha-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.