16886-09-2Relevant academic research and scientific papers
1,4-pentadienyl-3-sulfonamides: frameworks for disfavored radical cascade cyclizations.
Bommezijn,Martin,Kennedy,Lizos,Murphy
, p. 3405 - 3407 (2001)
[reaction: see text]. 1,4-pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.
An efficient two-step synthesis of 3-allylindoles
Kulkarni, Mukund G.,Davawala, Saryu I.,Dhondge, Attrimuni P.,Gaikwad, Dnyaneshwar D.,Borhade, Ajit S.,Chavhan, Sanjay W.
, p. 1003 - 1005 (2006)
A two-step synthetic sequence for an efficient synthesis of 3-allylindoles is described.
Sodium Perborate: A Facile Catalyst for Allylation of Active Centers
Jayaprakash, Soora Harinath,Krishna, Balam Satheesh,Prasad, Sthanikam Siva,Sudha, Sarva Santhi,Reddy, Cirandur Suresh
, p. 355 - 362 (2015)
An efficient and ecofriendly allylation of O-H, N-H, and C-H groups has been achieved successfully with the reaction of allyl bromide by using sodium perborate as a new catalyst in aqueous media. The advantage of this method is operationally simple, short reaction time, good yield, and simple workup conditions over the previously reported conventional methods such as amination, oxyalkylation reactions of allyl bromide, and Friedel-Crafts allylation chemistry.
Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane
Kimura, Masanari,Futamata, Makoto,Mukai, Ryutaro,Tamaru, Yoshinao
, p. 4592 - 4593 (2005)
Under palladium catalysis, Et3B nicely promotes allyl alcohols to undergo C3-selective allylation of indoles and tryptophan; the yields range 75-95%. Copyright
Zinc-mediated Barbier reactions of pyrrole and indoles: A new method for the alkylation of pyrrole and indoles
Yadav,Reddy,Reddy, P.Muralikrishna,Srinivas
, p. 5185 - 5187 (2002)
Pyrrole and indoles react smoothly with alkyl halides such as allyl bromide, prenyl bromide, crotyl bromide and propargyl bromide in the presence of zinc metal in THF to afford the corresponding 3- and 2-alkyl pyrrole and 3-alkyl indole derivatives in good yields with high regioselectivity.
Rapid Assembly of Functionalised Spirocyclic Indolines by Palladium-Catalysed Dearomatising Diallylation of Indoles with Allyl Acetate
Dhankher, Persis,Benhamou, Laure,Sheppard, Tom D.
, p. 13375 - 13381 (2014)
Herein, we report the application of allyl acetate to the palladium-catalysed dearomatising diallylation of indoles. The reaction can be carried out by using a readily available palladium catalyst at room temperature, and can be applied to a wide range of substituted indoles to provide access to the corresponding 3,3-diallylindolinines. These compounds are versatile synthetic intermediates that readily undergo Ugi reactions or proline-catalysed asymmetric Mannich reactions. Alternatively, acylation of the 3,3-diallylindolinines with an acid chloride or a chloroformate, followed by treatment with aluminium chloride, enables 2,3-diallylindoles to be prepared. By using ring-closing metathesis, functionalised spirocyclic indoline scaffolds can be accessed from the Ugi products, and a dihydrocarbazole can be prepared from the corresponding 2,3-diallylindole.
Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction
Kamijo, Shin,Yamamoto, Yoshinori
, p. 11940 - 11945 (2002)
The palladium-catalyzed three-component coupling reaction (TCCR) of aryl isocyanides, allyl methyl carbonate, and trimethylsilyl azide was conducted in the presence of Pd2(dba)3·CHCl3 (2.5 mol %) and dppe (1,2-bis(diphenyl
A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole
Tseng, Yi-Lun,Liang, Min-Chieh,Chen, I-Chia,Wu, Yen-Ku
, p. 609 - 612 (2018)
A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.
Alkene synthesis by photocatalytic chemoenzymatically compatible dehydrodecarboxylation of carboxylic acids and biomass
Nguyen, Vu T.,Nguyen, Viet D.,Haug, Graham C.,Dang, Hang T.,Jin, Shengfei,Li, Zhiliang,Flores-Hansen, Carsten,Benavides, Brenda S.,Arman, Hadi D.,Larionov, Oleg V.
, p. 9485 - 9498 (2019/10/11)
Direct conversion of renewable biomass and bioderived chemicals to valuable synthetic intermediates for organic synthesis and materials science applications by means of mild and chemoselective catalytic methods has largely remained elusive. Development of artificial catalytic systems that are compatible with enzymatic reactions provides a synergistic solution to this enduring challenge by leveraging previously unachievable reactivity and selectivity modes. We report herein a dual catalytic dehydrodecarboxylation reaction that is enabled by a crossover of the photoinduced acridine-catalyzed O-H hydrogen atom transfer (HAT) and cobaloxime-catalyzed C-H-HAT processes. The reaction produces a variety of alkenes from readily available carboxylic acids. The reaction can be embedded in a scalable triple-catalytic cooperative chemoenzymatic lipase-acridine-cobaloxime process that allows for direct conversion of plant oils and biomass to long-chain terminal alkenes, precursors to bioderived polymers.
Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis
Schwarz, J. Luca,Sch?fers, Felix,Tlahuext-Aca, Adrian,Lückemeier, Lukas,Glorius, Frank
supporting information, p. 12705 - 12709 (2018/10/09)
Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)-H bonds and thus significantly extends the scope of the venerable Nozaki-Hiyama-Kishi reaction.
