Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4748 - 4756
Опубликована: Янв. 1, 2024
Difunctionalizations of unactivated olefins with fluoroalkyl carboxylic acids or aldehydes via a radical-mediated functional group migration strategy are herein reported.
Язык: Английский
Nature Chemistry, Год журнала: 2023, Номер 15(12), С. 1683 - 1692
Опубликована: Ноя. 13, 2023
Язык: Английский
Процитировано
77
ACS Catalysis, Год журнала: 2023, Номер 13(3), С. 1678 - 1685
Опубликована: Янв. 13, 2023
We report a photoinduced iron/copper dual-catalytic strategy for the radical decarboxylation functionalization of aliphatic carboxylic acids. The ligand-to-iron charge transfer process under light was initially occurred to generate an unstabilized alkyl radical, and copper catalyst delivered enabled subsequent coupling reactions form C–N or C–C bonds. By merging iron-catalyzed with catalysis, this system allows smooth conversion wide range acids amination, decarboxylative dehydrogenation, alkylation efficiently. A variety complex drug natural molecules is applicable, suggesting that would facilitate rapid compound library synthesis benefit discovery pharmaceutical agents.
Язык: Английский
Процитировано
67
Chem, Год журнала: 2023, Номер 9(6), С. 1610 - 1621
Опубликована: Май 4, 2023
Язык: Английский
Процитировано
51
ACS Catalysis, Год журнала: 2024, Номер 14(3), С. 1300 - 1310
Опубликована: Янв. 11, 2024
Directly utilizing abundant and inexpensive sources of aliphatic carboxylic acids is highly attractive for the synthesis CF2H- CH3-containing compounds. Herein, we report a versatile photoinduced iron-catalyzed platform hydrodifluoromethylation hydromethylation alkenes without need additional stoichiometric oxidants. These two transformations are accomplished by visible-light-induced ligand-to-iron charge transfer open-shell activation system using industrial chemical difluoroacetic acetic as precursors postulated to operate via difluoromethyl methyl radical-mediated decarboxylation mechanism. Experimental results show that strategy also applicable difunctionalization unactivated alkenes. Meanwhile, this provides viable route pharmaceutically active molecules containing deuterated units. The protocol exhibits several features, including mild reaction conditions, divergent radical precursors, operational simplicity scalability, good chemo- regioselectivity, scalability supported continuous flow technology, ability provide high-value building blocks applications in one step.
Язык: Английский
Процитировано
38
Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(24), С. 4189 - 4230
Опубликована: Дек. 3, 2022
Abstract In the quest for sustainable processes, selection of resources and catalysts is central importance. Carboxylic acids, which are abundant, stable ideally biobased feedstocks, can be considered as attractive platforms towards a range functionalized molecules. A recent resurgence photoinduced ligand‐to‐metal charge transfer (LMCT) carboxylates led to tremendous developments in field earth‐abundant metal mediated, visible‐light induced (non)‐decarboxylative transformations carboxylic acids. These reactions combine use available starting materials, low‐consuming energy source abundant catalysts. Besides these undeniable advantages, they also provide mild, highly selective innovative conditions complex molecule functionalization. The objective this review give an overview advances LMCT with special focus on mechanistic aspects transformations. magnified image
Язык: Английский
Процитировано
53
Chemical Science, Год журнала: 2022, Номер 13(45), С. 13611 - 13616
Опубликована: Янв. 1, 2022
Sulfoximines are synthetically important scaffolds and serve roles in drug discovery. Currently, there is no solution to decarboxylative sulfoximination of benzoic acids; although thoroughly investigated, limited substrate scope harsh reaction conditions still hold back traditional thermal aromatic functionalization. Herein, we realize the first acids via photo-induced ligand copper charge transfer (copper-LMCT)-enabled carbometalation. The transformation proceeds under mild conditions, has a broad scope, can be applied late-stage functionalization complex small molecules.
Язык: Английский
Процитировано
45
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4764 - 4773
Опубликована: Янв. 1, 2023
A photo-induced iron-catalyzed strategy that facilitates the transformation of carboxylic acids and hydrocarbons into thioethers sulfoxides is herein reported.
Язык: Английский
Процитировано
31
Coordination Chemistry Reviews, Год журнала: 2023, Номер 500, С. 215522 - 215522
Опубликована: Ноя. 9, 2023
Язык: Английский
Процитировано
27
Organic Letters, Год журнала: 2024, Номер 26(5), С. 1110 - 1115
Опубликована: Янв. 26, 2024
Despite the significant success of decarboxylative radical reactions, catalytic systems vary considerably upon different acceptors, requiring renewed case-by-case reaction optimization. Herein, we developed an iron condition that enables highly efficient decarboxylation various carboxylic acids for a range transformations. This operationally simple protocol was amenable to wide array delivering structurally diverse oxime ethers, alkenylation, alkynylation, thiolation, and amidation products in useful excellent yields (>40 examples, up 95% yield).
Язык: Английский
Процитировано
16
Organic Letters, Год журнала: 2024, Номер 26(12), С. 2381 - 2386
Опубликована: Март 15, 2024
Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.
Язык: Английский
Процитировано
15