Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6507 - 6511
Published: July 18, 2024
Alkynones are valuable compounds with applications in various areas. In this work, we developed an efficient carbonylation procedure for the carbonylative cross-coupling of aryl thianthrenium salts aromatic alkynes. Various useful alkynones were produced moderate to excellent yields under mild conditions. Notably, among tolerated functional groups, bromide group can be maintained, which is ready further coupling reactions.
Language: Английский
Citations
7
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 13557 - 13566
Published: Aug. 28, 2024
The incorporation of the difluoromethyl (CF2H) group into arenes has increasingly been recognized as important in drug discovery. Herein, we report a divergent cross-coupling method for constructing both aryl difluoromethanes and difluoroketones from thianthrenium salts. Site selectivity Negishi-type coupling C1 insertion reactions was achieved under palladium catalysis. Both transformations proceed with broad functional tolerance, enabling late-stage difluoromethylation difluoromethylcarbonylation complex molecules. synthetic utility this demonstrated by synthesizing four pharmaceutical analogues same precursor applying it downstream functionalization difluoroketones.
Language: Английский
Citations
7
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 30, 2024
We report here a step-economic and cost-effective cross-electrophile coupling of aryl thianthrenium salts with widely available bromides, which proceeded effectively via C-S bond activation at ambient temperature in THF the presence palladium catalyst, magnesium turnings, lithium chloride to enable facile assembly wide array structurally diverse biaryls modest good yields functional group compatibility. In addition, gram-scale reaction could also be realized.
Language: Английский
Citations
4
Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111225 - 111225
Published: April 1, 2025
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: June 3, 2024
A dearomative oxidation of pyrroles to Δ
Language: Английский
Citations
2
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 9, 2024
Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes benzyl acetylene toward alkynones furanones. Various desired products were prepared in good yields broad functional group tolerance including the bromide group. In case using acetylene, corresponding furanones can be obtained under same conditions two molecules CO inserted.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12508 - 12513
Published: Aug. 13, 2024
Thioesters make up an important class of bioactive compounds. Due to their chemoselectivity, they have been widely used in the synthesis a wide range complex molecules and natural products. At present, chemists developed variety methods for preparation thioester However, these usually require use transition metal catalysis or harsh reaction conditions. The strategy synthesizing compounds via visible light-induced electron donor–acceptor (EDA) reactions avoids problems associated with conventional through development photocatalysis. Here we report sustainable method thiocarbonylating aryl sulfonium salts EDA process without metals.
Language: Английский
Citations
1
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: June 3, 2024
Abstract A dearomative oxidation of pyrroles to Δ 3 ‐pyrrol‐2‐ones is described, which employs a sulfoxide as oxidant, in conjunction with carboxylic acid anhydride and Brønsted additive. 3‐substituted undergo regioselective give the product isomer oxygen has been introduced at more hindered position. Regioselectivity rationalized by proposed mechanism that proceeds initial thianthrenium introduction less‐hindered pyrrole α‐position, followed distal attack an nucleophile subsequent elimination thianthrene. The same reaction conditions are also able effect chemoselective indoles indolin‐3‐ones additionally 2‐hydroxyindolin‐3‐ones. Here again, regio‐ chemoselectivities through intermediacy salt.
Language: Английский
Citations
0
Green Chemistry, Journal Year: 2024, Volume and Issue: 26(23), P. 11686 - 11694
Published: Jan. 1, 2024
This paper describes a new method for the activation of aryl radicals via EDA complexes without metals and photosensitizers carbonylation with various nucleophilic reagents under visible light.
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.
Language: Английский
Citations
0