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Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes

A mild, practical protocol for the decarboxylative alkylation of heteroarenes has been accomplished via iron photocatalysis. A diverse range of carboxylic acids readily undergo oxidative decarboxylation and then couple with a broad array of heteroarenes in this transformation. The photoexcited state lifetimes of iron complexes are typically much shorter than those of iridium and ruthenium complexes. Here we describe our effort on iron photocatalysis by utilizing the intramolecular charge transfer pathway of iron-carboxylate complexes.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes

A mild, practical protocol for the decarboxylative alkylation of heteroarenes has been accomplished via iron photocatalysis. A diverse range of carboxylic acids readily undergo oxidative decarboxylation and then couple with a broad array of heteroarenes in this transformation. The photoexcited state lifetimes of iron complexes are typically much shorter than those of iridium and ruthenium complexes. Here we describe our effort on iron photocatalysis by utilizing the intramolecular charge transfer pathway of iron-carboxylate complexes.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Extracurricular laboratory:new discovery of Tetrahydro-2H-pyran-2-carboxylic acid

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Conformational memory in enantioselective radical reductions and a new radical clock reaction

The radical decarboxylation of acid 1 led to tetrahydropyran 3 with significant optical activity. This transfer of chirality is an example of a conformational memory effect and derives from the slow ring inversion of the atropisomer 2 and its enantiomer 2′. A similar conformational memory effect was observed in the reductive decyanation and reductive lithiation of cyanohydrin 4. We propose that the racemization of radicals with chiral conformations such as 2 could be used as new radical clocks. The rate of racemization of 2 was evaluated and used to determine the rate of H atom transfer to 2 by different H atom donors. The rate of racemization of 2 is 5.7 x 108 s-1 at 22 C, which is about five times faster than ring opening of a cyclopropylmethyl radical.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Top Picks: new discover of 51673-83-7

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Use of a conformational radical clock for evaluating alkyllithium-mediated cyclization reactions

matrix presented The reductive lithiation of nitrile 9 led to the cyclic product 11 as a single diastereomer in 42% ee. The intermediate radical is a conformational radical clock. The radical lifetime can be determined from the optical purity of the product 11. We show that the lifetime of the intermediate radical is too brief to allow a radical cyclization, and thus the cyclization proceeds through an alkyllithium intermediate.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Decarboxylative C?C and C?N Bond Formation by Ligand-Accelerated Iron Photocatalysis

The photoexcited state lifetimes of iron complexes are typically much shorter than those of iridium and ruthenium complexes. For that reason, iron complexes find less application in photochemical organic synthesis. Through iron photocatalysis, a mild and effective protocol for decarboxylative C?C and C?N bond formation has been achieved. The carboxylic acids readily undergo radical decarboxylation in the presence of Fe2(SO4)3 and di-(2-picolyl)amine under visible light irradiation. The resulting alkyl radicals then react with Michael acceptors or azodicarboxylates to furnish the adducts.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Palladium-Catalyzed Directed C(sp3)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach

Saturated heterocycles, such as THFs, pyrrolidines, piperidines and THPs, are essential components of many biologically active compounds. Examples of C-H functionalization on these important ring systems remain scarce, especially at unactivated positions. Here we report the development of conditions for the palladium-catalyzed stereoselective C(sp3)-H arylation at unactivated 3-positions of 5- and 6-membered N- and O-heterocycles with aminoquinoline directing groups. Subtle differences in substrate structures altered their reactivity significantly; and different conditions were required to achieve high yields in each case. Successful conditions were developed using a short empirical optimization approach to cover reaction space with a limited set of variables. Excellent cis-selectivity was achieved in all cases, except for the THP substrate where minor trans-products were formed through a different palladacyclic intermediate. Here, differences in reactivity and selectivity with other directing groups were examined.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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COMPOSITIONS AND METHODS OF MAKING EXPANDED HEMATOPOIETIC STEM CELLS USING DERIVATIVES OF FLUORENE

This invention is directed to, inter alia, compounds, methods, systems, and compositions for the maintenance, enhancement, and expansion of hematopoietic stem cells derived from one or more sources of CD34+ cells. Sources of CD34+ cells include bone marrow, cord blood, mobilized peripheral blood, and non-mobilized peripheral blood. Also provided herein are compounds of Formula I which are useful in maintaining, enhancing, and expanding of hematopoietic stem cells.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with ethynylbenziodoxolone (EBX) reagents allowed the decarboxylative alkynylation of carboxylic acids in good yields under mild conditions. The method could be applied to silyl-, aryl-, and alkyl- substituted alkynes. It was particularly successful in the case of alpha-amino and alpha-oxo acids derived from biomass.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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HETEROCYCLIC AMIDE COMPOUND

Provided is a heterocyclic amide compound that may have a PRS inhibitory action and is expected to be useful as a prophylactic or therapeutic agent for PRS associated diseases and the like including cancer. A compound represented by the following formula (I): wherein a group represented by is a group represented by the following formula (II) or the following formula (III): and other symbols are as described in the DESCRIPTION, or a salt thereof.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Final Thoughts on Chemistry for Tetrahydro-2H-pyran-2-carboxylic acid

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Substituted Pyrrolidines and Methods of Use

The invention discloses compounds of Formula (I) wherein R1, R2, R2A, R3, R3A, R4, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics