5452-02-8Relevant articles and documents
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters
Wang, Lin,Neumann, Helfried,Spannenberg, Anke,Beller, Matthias
supporting information, p. 7469 - 7472 (2017/07/12)
An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.
PALLADIUM-CATALYZED DOUBLE CARBONYLATION REACTIONS OF ARYL HALIDES AFFORDING α-KETO ESTERS
Ozawa, Fumiyuki,Kawasaki, Nobuo,Yamamoto, Takakazu,Yamamoto, Akio
, p. 567 - 570 (2007/10/02)
Various aryl iodides can be converted into α-keto esters in reactions with carbon monoxide and alcohols in the presence of tertiary amines and catalytic amounts of tertiary phosphine-coordinated palladium complexes.