TY - JOUR
T1 - Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper
AU - Berk, Scott C.
AU - Yen, Ming Chang P.
AU - Jeong, Nakcheol
AU - Knochel, Paul
PY - 1990
Y1 - 1990
N2 - The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.
AB - The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.
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U2 - 10.1021/om00162a016
DO - 10.1021/om00162a016
M3 - Article
AN - SCOPUS:0000840453
VL - 9
SP - 3053
EP - 3064
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 12
ER -