Science of Synthesis

Heaney, H.; Christie, S., Science of Synthesis, (2004) 3, 598.

Lipshutz has also outlined potential alternatives to the thienyl ligand: 1H-imidazolyl and 1H-pyrrolyl (‌Scheme 438‌).[‌1556‌] These were introduced to circumvent the use of thiophene on a large scale. They are prepared in a similar manner to the thienyl derivative: reaction of the hetereocycle with butyllithium, followed by introduction of copper(I) cyanide. These intermediates are not quite as stable as the thienylcopper species, but can be stored for extended periods. Again, introduction to these of a second nucleophilic group provides a mixed cuprate which is capable of undergoing the usual copper chemistry. Interestingly, when a non-aromatic amine, pyrrolidine, was employed standard copper chemistry was shut down, showing the type of ligand is important in the copper reagent.

‌Meeeee 888‌ Meeeeeeee- eee Meeeeee-Meeeeee Meeee Meeeeeeeeeeee[‌8888‌]

‌Meeeee 888‌ eeeee eeee eeee eeeee eeeeeeee ee eeeeeee eee eeeee eeeeee eeeeeeeee ee eeee ee eeee eeeee. Meeeeee eeee eeee eee eee eeeeeeee ee eee eeee eee eeeeeeeeee eeeeeeeee eeeeeeeeee eeeeeee ee ee eeee.

‌Meeeee 888‌ Meeeeeeee ee Meeeeeeee-Meeee Meeee Meeeeeeeeeeee[‌8888‌]

References