Lithium Complexes in Organic Synthesis

Synthesis and DFT analysis of non-covalent interactions in crystal structures of 6-R-2-alkoxy-, 2,3-di-, and 2,2,3-tri-tert-butylpyrrolo[1,2-b][1,2,4]triazines

“…tert -Butyl carboxylate 2b was significantly more stable towards transesterification and reacted with n -BuOH/K 2 CO 3 under analogous conditions to afford the expected compound 2c (Scheme 2 ) [ 16 ]. Heterocycle 2b also reacted with t -BuLi at low temperature (THF, –100 °C) to selectively give the aromatic 2,3-di- tert -butyl pyrrolotriazine 4b, along with a small amount of by-product 4a as a result of hydride transfer reduction [ 32 , 33 ] (Scheme 3 ). XRD data for 2c and 4a were previously described in literature [ 16 , 19 ].…”

Unlocking geminal fluorohaloalkanes in nucleophilic fluoroalkylation chemistry: generation and trapping of lithiumfluorocarbenoids enabled by flow microreactors

“…This strategy involves fluorinated lithium carbenoids generated via lithium/iodine exchange reaction starting from 1-fluoro-1-iodoalkanes followed by coupling with suitable electrophilic partners. 20 Iodine was selected as the best halogen as it assures a fast Li/I exchange reaction, crucial in this process involving a short living fluorocarbenoid. It is worth pointing out that the main issue of this apparently simple synthetic logic is the expected very high thermal and chemical instability of the lithium fluoroalkyl carbenoid.…”