20432-26-2Relevant articles and documents
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Campbell,Young
, p. 3066 (1947)
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Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent
Gao, Mingjie,Jia, Xiaofei,Lv, Jinhe,Ren, Xinyi,Song, Jiaxin,Xie, Congxia,Zhang, Jinrong,Zhang, Kai,Zhao, Jinyu,Zhou, Ziqin,Zong, Lingbo
, p. 4708 - 4713 (2021/07/26)
A sulfoxantphos modified palladium-catalyzed synthesis of α,β-unsaturated carboxylic acids from alkynes with CO and H2O was described. The atom-economic hydroxycarbonylation of various symmetrical and unsymmetrical alkynes can be achieved with chemo-, stereo-, and regioselectivity, affording the corresponding carboxylic acids in good to excellent yields. Using water as the reaction solvent, the water-soluble palladium catalyst was easily separated from the product and could be reused for 5 cycles.
The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes with formic acid as a CO surrogate as well as a hydrogen source: An alternative indirect utilization of CO2
Chen, Kai-Hong,He, Liang-Nian,Qiu, Li-Qi,Xia, Shu-Mei,Yang, Zhi-Wen,Yao, Xiang-Yang
supporting information, p. 8089 - 8095 (2021/11/01)
An unprecedented strategy has been developed involving the earth-abundant Cu-catalyzed hydrocarboxylation of alkynes with HCOOH to (E)-acrylic derivatives with high regio- and stereoselectivity via synergistic effects with ppm levels of a Pd catalyst. Both symmetrical and unsymmetrical alkynes bearing various functional groups were successfully hydrocarboxylated with HCOOH, and the modification of a pharmaceutical molecule exemplified the practicability of this process. This protocol employs HCOOH as both a CO surrogate and hydrogen donor with 100% atom economy and it can be viewed as an alternative approach for indirect CO2 utilization. Mechanistic investigations indicate a Cu/ppm Pd cooperative catalysis mechanism via alkenylcopper species as potential intermediates formed from Cu-hydride active catalytic species with HCOOH as a hydrogen source. This bimetallic system involving inexpensive Cu and trace Pd provides a reliable and efficient hydrocarboxylation method to access industrially useful acrylic derivatives with HCOOH as a hydrogen source, and it provides novel clues for optimizing other Cu-H-related co-catalytic systems.
