65246-40-4

Upstream product

• 1245573-31-2 2-(2-bromophenyl)-1-(4-tert-butylphenyl)ethanone 
• 14714-50-2 2-hydroxybenzyl cyanide 
• 1309071-13-3 2-((4-(tert-butyl)phenyl)ethynyl)cyclohex-2-enone 
• 95-56-7 2-hydroxybromobenzene 
• 772-38-3 4-tert-Butylphenylacetylene 
• 533-58-4 2-Iodophenol 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 85614-50-2 1-(benzofuran-2-yl)butan-1-one 
• 98437-24-2 benzofuran-2-boronic acid 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 91703-34-3 2-(β,β-dibromovinyl)phenol 
• 1313026-14-0 C₁₃H₁₂BNO₅ 
• 3972-65-4 1-bromo-4-tert-butylbenzene 

Relevant academic research and scientific papers

One-pot Tandem Heck alkynylation/cyclization reactions catalyzed by Bis(Pyrrolyl)pyridine based palladium pincer complexes

Ligand assisted palladium catalyzed one-pot tandem Heck alkynylation/cyclization reactions for the synthesis of benzofurans was reported in this paper. Well-defined palladium-pincer complexes exhibited excellent catalytic activities for the one-pot tandem Heck alkynylation/cyclization reactions yielding benzofuran derivatives using 0.1 molpercent catalyst. All the catalytic reactions are performed in air. The effects of variables such as solvents, the temperature on the catalytic activity are also reported. High product conversion was obtained for differently substituted 2-iodophenol at 120 °C in 10 h.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate

A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.

Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole

Well-defined and air-stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis-N-heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2-iodophenol with a variety of terminal alkynes and C-H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air-stable palladium-NHC complexes were characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis-N-heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2-iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C-H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co-catalyst.

Transition-metal-free base catalyzed intramolecular cyclization of 2-ynylphenols for efficient and facile synthesis of 2-substituted benzo[b]furans

A transition-metal-free base catalyzed intramolecular cyclization of 2-ynylphenols was developed for the facile synthesis of 2-substituted benzo[b]furans. Various 2-aryl and 2-alkyl substituted benzo[b]furans can be obtained with good to excellent yields

Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors

The nitrosonium ion-catalyzed dehydrogenative coupling of heteroarenes under mild reaction conditions is reported. The developed method utilizes ambient molecular oxygen as a terminal oxidant, and only water is produced as byproduct. Dehydrogenative coupl

1,2,3-Triazole based bisphosphine, 5-(diphenylphosphanyl)-1-(2-(diphenylphosphanyl)-phenyl)-4-phenyl-1: H -1,2,3-triazole: An ambidentate ligand with switchable coordination modes

The reaction of 1-(2-bromophenyl)-4-phenyl-1H-1,2,3-triazole (1) with Ph2PCl yielded bisphosphine, 5-(diphenylphosphanyl)-1-(2-(diphenylphosphanyl)phenyl)-4-phenyl-1H-1,2,3-triazole (2). Bisphosphine 2 exhibits ambidentate character in either the κ2-P,N or κ2-P,P coordination mode. Treatment of 2 with [M(CO)4(piperidine)2] (M = Mo and W) yielded κ2-P,N and κ2-P,P coordinated Mo0 and W0 complexes [M(CO)4(2)] [M = W-κ2-P,N (4); Mo-κ2-P,P (5); W-κ2-P,P (6)] depending on the reaction conditions. Formation and stability of κ2-P,P coordinated Mo0 and W0 complexes were assessed by time dependent 31P{1H} NMR experiments and DFT studies. The complex 4 on treatment with [AuCl(SMe2)] afforded the hetero-bimetallic complex [μ-PN,P-{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2AuCl)}-κ2-P,N}W(CO)4] (7). The 1:1 reaction between 2 and [CpRu(PPh3)2Cl] yielded [(η5-C5H5)RuCl{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-κ2-P,P] (8), whereas the similar reaction with [Ru(η6-p-cymene)Cl2]2 in a 2:1 molar ratio produced a cationic complex [(η6-p-cymene)RuCl{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-κ2-P,N]Cl (9). Similarly, treatment of 2 with [M(COD)(Cl)2] (M = Pd and Pt) in a 1:1 molar ratio yielded PdII and PtII complexes [{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}-κ2-P,P}PdCl2] (10) and [{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}-κ2-P,P}PtCl2] (11). The reaction of 2 with 2 equiv. of [AuCl(SMe2)] afforded [Au2Cl2{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-μ-P,P] (12). Most of the complexes have been structurally characterized. Palladium complex 10 shows excellent catalytic activity towards Cu-free Sonogashira alkynylation/cyclization reactions.

Palladium nanoparticles catalyzed synthesis of benzofurans by a domino approach

Abstract Palladium nanoparticles (PdNPs) were used as a catalyst for the one-pot synthesis of a variety of benzofurans by Sonogashira cross-coupling reactions under ambient conditions. The catalyst could be recycled without significant loss in its activity.

Copper pincer complexes as advantageous catalysts for the heteroannulation of ortho-halophenols and alkynes

A new, non-symmetrical copper(II) pincer complex catalyzes much more efficiently the formation of benzofuran by the reaction between ortho-iodophenols and alkynes. The lowest catalyst loadings are realized for this reaction, and bromo- and chlorophenols are heteroannulated for the first time. Strong evidence for hydrophenoxylation and intramolecular halogen atom-transfer steps catalyzed by this remarkably active, recyclable homogeneous catalyst is provided.

Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: One-pot synthesis of 2-arylbenzofurans

The first example of the palladium-catalyzed one-pot synthesis of 2-arylbenzofurans in moderate to excellent yields via a tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates is reported. A plausible mechanism for the formation of 2-arylbenzofurans involving desulfinative addition and intramolecular annulation reactions is proposed. Moreover, the present synthetic route to benzofurans could be readily scaled up to the gram quantity without any difficulty. Thus, the method represents a convenient and practical strategy for synthesis of benzofuran derivatives. This journal is the Partner Organisations 2014.