Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(7), P. 1378 - 1385
Published: Jan. 1, 2024
An efficient transition-metal/photocatalyst-free visible-light-driven one-pot three-component reaction between thianthrenium salts, carbon disulfide and amines under air atmosphere for the preparation of S -aryl dithiocarbamates is developed.
Language: Английский
Chem, Journal Year: 2024, Volume and Issue: 10(4), P. 1240 - 1251
Published: Feb. 13, 2024
The photoactivation of sulfonium salt EDA (electron donor-acceptor) complexes provides a mild platform for aryl-radical-mediated halogen atom transfer activation wide range functionalized alkyl iodides, including tertiary iodides. Using an aryl with carbonate as inexpensive donor complex formation, the general reaction has been applied in divergent, metal-free photochemical approach to nitriles and amides. This divergency was made possible by tuning isocyanide radical traps. For example, identification readily accessible, bench-stable, crystalline amide containing grants access nitrile products complete selectivity.
Language: Английский
Citations
16
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(25)
Published: April 16, 2024
The one-pot synthesis of λ
Language: Английский
Citations
12
Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 5938 - 5943
Published: Jan. 1, 2024
Cyclopropyl-substituted sulfonium salts are obtained by Rh-catalysed addition of α-diazo dibenzothiophenium to olefins. When indenes used as substrates, initially formed cyclopropyl rings open with concomitant elimination dibenzothiophene, enabling access 2-substituted naphthalenes.
Language: Английский
Citations
11
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4318 - 4342
Published: Jan. 1, 2024
This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.
Language: Английский
Citations
9
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1294 - 1304
Published: Jan. 7, 2025
Given the widespread presence of spirocyclic scaffolds in natural products and pharmacologically relevant synthetic compounds, development efficient methodologies for their construction holds great importance medicinal chemistry pharmaceutical research. In this study, a general photochemical dearomative spirocyclization nonactivated arenes has been established. The key to method lies ability amine-borane radicals activate aryl bromides iodides via halogen-atom transfer, thereby allowing conversion halides into corresponding subsequent chemodivergent transformations. remarkable compatibility versatility 1,4-difunctionalization is showed by rapid assembly structurally diverse 1,4-cyclohexadiene-based spirocycles incorporating oxindole, indoline, or dihydrobenzofuran subunits. Moreover, potential utility protocol exemplified formal total synthesis vasopressin V2 receptor antagonist Satavaptan.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 26, 2025
A photoinduced copper-mediated acyloxylation of arylthianthrenium or arylphenoxathiinium salts with either aliphatic aromatic carboxylic acids is described for the convenient synthesis O-aryl esters. The reaction has shown obvious advantages, such as high efficiency, good functional group tolerance, excellent chemoselectivity, and capacity esterification complex drug molecules, offering a practical synthetic route to multifunctionalized sterically congested esters, which are potentially useful in development new prodrugs twin drugs.
Language: Английский
Citations
1
Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 2, 2025
ConspectusDuring the past few years, interest among organic synthesis practitioners in use of sulfonium salts has exponentially growth. This can arguably be attributed to a series specific factors: (a) The recent development more direct and efficient protocols for these species, which make reagents wide structural variety easily available multigram scale. (b) recognition that reactivity resembles hypervalent iodine compounds, therefore, they used as effective replacement such species most their applications. (c) Their intrinsic thermal stability tolerance air moisture, clearly surpass I(III)-reagents analogue reactivity, facilitate purification, isolation well-defined storage, safely handling on larger (d) Finally, possibility further functionalize once sulfur-containing platform been incorporated. Specifically, this last synthetic approach is not trivial when working with I(III)-species facilitates access no counterpart I(III) realm.This renewed led improvement already existing transformations well discovery unprecedented ones; particular, by incorporate partners traditional cross-coupling C–H activation steps or combine them modern technologies photocatalysis electrosynthesis. In Account, originally prepared our laboratory will outlined compared I(III)-counterparts. Some are now commercially available, started spread widely across chemistry community, helping speed process identification potentially bioactive products new functionaliced materials. However, challenges still remain. characterized an optimal balance between site-selectivity, showing broader compatibility toward sensitive functional groups need. addition, often makes necessary (sophisticated) catalysts activate latent hidden structures. Although priori one see fact disadvantage, it might actually decisive harvest full potential because surely preparation operational context I(III)-chemistry. If becomes true, may contribute expediting retrosynthetic disconnections that, date, impossible.
Language: Английский
Citations
1
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2344 - 2351
Published: April 5, 2024
Abstract A process for the synthesis of aryl thioglycosides from thianthrenium salts and 1‐thiosugars is achieved by copper(I)‐mediated, photoredox‐catalyzed reactions. The desired products could be obtained in 32% to 78% yield after irradiation with 34 W blue light at room temperature. Various functional groups, especially including halogen were well tolerated under standard reaction conditions. This strategy differs conceptually all previous S ‐glycosylations that thiosugar functionality incorporated into complex natural or drugs a late stage site‐selectively, which has not been shown via halides aryldiazonium salts.
Language: Английский
Citations
7
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2587 - 2595
Published: April 19, 2024
Abstract A photochemical synthesis of biologically relevant benzyl oxindoles is presented via electron‐donor acceptor (EDA) complex strategy. This exogenous photocatalyst‐free method describes the formation a new electron donor‐acceptor based on potassium carbonate and thianthrenium salts for C( sp 2 )−C( 3 ) bond formation. transition‐metal free reaction allows rapid increase in molecular complexity chemical space, tolerating different functional groups as well sophisticated biomolecules. The scalability sustainability this highlighted by an important waste recovery protocol. Mechanistic investigations support EDA that induces radical chain, applicability showcased straightforward derivatization reactions.
Language: Английский
Citations
7
Chemical Communications, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Recent years have witnessed the emergence of direct intermolecular C(sp
Language: Английский
Citations
7