60573-59-3Relevant articles and documents
Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis
Liu, Kun,Studer, Armido
supporting information, p. 4903 - 4909 (2021/05/04)
N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.
Deoxygenation of carbonyl compounds using an alcohol as an efficient reducing agent catalyzed by oxo-rhenium complexes
Bernardo, Joana R.,Fernandes, Ana C.
supporting information, p. 2675 - 2681 (2016/05/24)
This work describes the first methodology for the deoxygenation of carbonyl compounds using an alcohol as a green solvent/reducing agent catalyzed by oxo-rhenium complexes. The system 3-pentanol/ReOCl3(SMe2)(OPPh3) was successfully employed in the deoxygenation of several aryl ketones to the corresponding alkenes and also in the deoxygenation of aryl aldehydes to alkanes with moderate to excellent yields. The catalyst ReOCl3(SMe2)(OPPh3) can also be used in several catalytic cycles with good activity.
Dioxomolybdenum Complexes as Excellent Catalysts for the Deoxygenation of Aryl Ketones to Aryl Alkenes
Fernandes, Tiago A.,Fernandes, Ana C.
, p. 3503 - 3507 (2015/11/10)
This work describes a new methodology for the selective deoxygenation of aryl ketones to the corresponding aryl alkenes catalyzed by dioxomolybdenum complexes using silanes as reducing agents. The best results were obtained with the system PhSiH3/MoO2Cl2(H2O)2 (5-10 mol %), which was very efficient for the deoxygenation of a large variety of aryl ketones to alkenes in excellent yields. This new methodology has the advantages of using an inexpensive, environmentally friendly, easily prepared, and air-stable catalyst in ether solution.