Palladium Acetate/[CPy][Br]: An Efficient Catalytic System towards the Synthesis of Biologically Relevant Stilbene Derivatives via Heck Cross‐Coupling Reaction.

Girase, Tejpalsingh Ramsingh; Patil, Kesharsingh J.; Kapdi, Anant R.; Gupta, Gaurav R.

doi:10.1002/slct.201904837

Cited by 15 publications

(2 citation statements)

References 142 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…196～198 ℃; 1 H NMR (500 MHz, CDCl 3 ) δ: 9.04 (s, 1H), 8.07～8.05 (m, 2H), 7.85 (d,J＝16.5 Hz,1H),7.77～ 7.74 (m,1H),7.71～7.68 (m,1H),7.56 (d,J＝8.0 Hz,2H),7.34 (d,J＝16.5 Hz,1H),7.26～7.23 (m,2H), 2.40 (s, 3H); 13 C NMR (125.4 MHz, CDCl 3 ) δ: 150. 7, 144.5, 142.5, 141.5, 139.5, 136.5, 133.3, 130.3, 129.7, 129.2, 127.5, 124.4, 21.4; MS (EI) m/z (%): 246 (30), 245 (51), 231 (18), 209 (13), 208 (21), 207 (100), 191 (14), 133 (14), 115 (11), 96 (16), 76 (7), 73 (22).…”

Section: General Informationmentioning

confidence: 99%

Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols

Liu,

Han,

et al. 2024

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

By performing the reactions in the presence of adequate amount of air and a suitable base, selective olefination of methyl N-heteroarenes with alcohols can be effectively achieved without using any external catalyst. Control experiments revealed that, with adequate air, base can promote the aerobic oxidation of alcohols almost completely to carbonyl intermediates, which then condense with the methyl N-heteroarenes to afford the alkenyl N-heteroarene products. As the reaction is performed with adequate amount of air and a lower loading of the base at a lower temperature than that of the alkylation reaction, the generated alkenyl N-heteroarenes cannot be transfer hydrogenated to the alkylated products by the remained small amount of alcohol in the reaction mixture, which leads to a high selectivity of the olefination reaction. This method is thus a practical way for preparation of the alkenyl N-heteroarenes, being a complementary method to previous transition metal-free C-alkylation reaction of methyl N-heteroarenes with alcohols in the presence of small amount of air.

show abstract

Section: General Informationmentioning

confidence: 99%

Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols

Liu,

Han,

et al. 2024

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

show abstract

“…[2] The Z/E configuration of olefin has a great influence on its properties. [3] At present, synthesis of thermodynamically stable E-olefins is well developed, which could be achieved via Wittig reactions, [4] cross-coupling reactions, [5] semihydrogenation of alkynes [6] and Peterson olefinations. [7] Synthesis of Z-olefins is rather limited.…”

Section: Introductionmentioning

confidence: 99%

Direct Irradiation of (E)‐Styrylpyridin‐2(1H)‐ones to (Z)‐Isomers with Visible Light

Sui

Zhang

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

The E to Z isomerization of styrylpyridin‐2(1H)‐ones was achieved through visible light (420 nm) irradiation in dioxane at ambient temperature. Driven by the visible light, (E)‐3‐styrylpyridin‐2(1H)‐ones, (E)‐4‐styrylpyridin‐2(1H)‐ones and (E)‐5‐styrylpyridin‐2(1H)‐ones in dioxane at room temperature under Argon atmosphere were successfully converted to the corresponding (Z)‐styrylpyridin‐2(1H)‐ones in good yields. The described E to Z photoisomerization of styrylpyridin‐2(1H)‐ones proceeded smoothly with the 420 nm blue light, avoided usage of photocatalysts, additives and are easy to operate.

show abstract

Substrate‐Controlled Product Divergence in Iron(III)‐Catalyzed Reactions of Propargylic Alcohols: Easy Access to Spiro‐indenyl 1,4‐Benzoxazines and 2‐(2,2‐Diarylvinyl)quinoxalines

Chowdhury

2023

Chemistry A European J

View full text Add to dashboard Cite

We report herein unprecedented cascade reactions of O-propargyl-N-tosyl-amino phenols with 10 mol% FeCl 3 in DCE at room temperature for 0.67-3 h to form spiro-indenyl 1,4-benzoxazines with 38-89 % yield. Replacing the substrates' oxygen atom by a N-tosylimine group followed by treatment with the same catalyst and solvent at 80 °C produced 2-(2,2-diarylvinyl)quinoxalines in 12-20 h with up to 62 % yield. Mechanistic understanding provided an insight into the transformations. The use of simple substrates and an environmentally benign low-cost catalyst, broad substrate scope and tolerance of diverse functional groups makes the methodology inherently attractive.

show abstract

Palladium Acetate/[CPy][Br]: An Efficient Catalytic System towards the Synthesis of Biologically Relevant Stilbene Derivatives via Heck Cross‐Coupling Reaction.

Cited by 15 publications

References 142 publications

Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols

Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols

Direct Irradiation of (E)‐Styrylpyridin‐2(1H)‐ones to (Z)‐Isomers with Visible Light

Substrate‐Controlled Product Divergence in Iron(III)‐Catalyzed Reactions of Propargylic Alcohols: Easy Access to Spiro‐indenyl 1,4‐Benzoxazines and 2‐(2,2‐Diarylvinyl)quinoxalines

Contact Info

Product

Resources

About