14301-08-7Relevant academic research and scientific papers
One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)–Copper(I) Iodide–Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction
Qiu, Shaozhong,Zhang, Caiyang,Qiu, Rui,Yin, Guodong,Huang, Jinkun
, p. 313 - 321 (2018)
The low loading combination of the complex [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand-free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single-step procedure. The unsymmetrical diarylalkynes can be obtained through a one-pot two-step approach. The reactions of aryl bromides with 1,4-bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4-diaryl-1,3-diynes in a similar fashion. This route to diarylalkynes and 1,4-diaryl-1,3-diynes is complementary to previously reported synthetic procedures. (Figure presented.).
Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes
Samantaray, Manoja K.,Shaikh, Mobin M.,Ghosh, Prasenjit
, p. 3477 - 3486 (2009)
Highly convenient copper-free and amine-free Sonogashira coupling of aryl bromides and iodides with terminal acetylenes under amenable conditions in air and in a mixed aqueous medium are reported using several new, user friendly and robust palladium precatalysts (1-5) of N/O-functionalized N-heterocyclic carbenes (NHCs). In particular, the precatalysts, 1 and 2, were synthesized from the imidazolium chloride salts by the treatment with PdCl2 in pyridine in presence of K2CO3 as a base while the precatalysts, 3-5, were synthesized from the respective silver complexes by the treatment with (COD)PdCl2. The DFT studies carried out on the 1-5 complexes suggest the presence of strong NHC-Pd σ-interactions arising out of deeply buried NHC-Pd σ-bonding molecular orbitals (MOs) that account for the inert nature of the metal-carbene bonds and also provide insights into the exceptional stability of these precatalysts.
Ni(acac)2/2,6-bis(diphenylphosphino)pyridine/CuI: A highly efficient palladium-free homogeneous catalyst for the Sonogashira cross-coupling reaction
Ataei, Ali,Daryanavard, Marzieh,Joshaghani, Mohammad,Rafiee, Ezzat
, (2020)
A highly efficient palladium-free homogeneous catalyst involving Ni(acac)2/2,6-bis(diphenylphosphino)pyridine ((Ph2P)2py)/CuI components was used for the Sonogashira cross-coupling reaction. The Sonogashira reaction was in
Palladium-tetraphosphine complex: An efficient catalyst for the coupling of aryl halides with alkynes
Feuerstein, Marie,Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 2235 - 2237 (2003)
A study was performed on palladium-tetraphosphine complex which is an efficient catalyst for the coupling of aryl halides with alkynes. It was found that a turnover number of 2600000 can be obtained for the reaction of 4-trifluoro-methylbromobenzene with phenylacetylene in the presence of this catalyst. It was also found that the catalyst is more efficient than the complex formed with a triphenylphosphine ligand.
Pd(PhCN)2Cl2/P(t-Bu)3: A versatile catalyst for Sonogashira reactions of aryl bromides at room temperature
Hundertmark, Thomas,Littke, Adam F.,Buchwald, Stephen L.,Fu, Gregory C.
, p. 1729 - 1731 (2000)
(matrix presented) Pd(PhCN)2Cl2/P(t-Bu)3 serves as an efficient and a versatile catalyst for room-temperature Sonogashira reactions of aryl bromides.
Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
Xu, Hui,Ma, Biao,Fu, Zunyun,Li, Han-Yuan,Wang, Xing,Wang, Zhen-Yu,Li, Ling-Jun,Cheng, Tai-Jin,Zheng, Mingyue,Dai, Hui-Xiong
, p. 1758 - 1764 (2021/02/09)
Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.
Charge stabilizationviaelectron exchange: excited charge separation in symmetric, central triphenylamine derived, dimethylaminophenyl-tetracyanobutadiene donor-acceptor conjugates
Yadav, Indresh S.,Alsaleh, Ajyal Z.,Misra, Rajneesh,D'Souza, Francis
, p. 1109 - 1120 (2021/02/06)
Photoinduced charge separation in donor-acceptor conjugates plays a pivotal role in technology breakthroughs, especially in the areas of efficient conversion of solar energy into electrical energy and fuels. Extending the lifetime of the charge separated
Ligand-Free and Recyclable Palladium(II) Acetate Catalyzes the Decarboxylative Cross-Coupling of Alkynyl Carboxylic Acids with Arylboronic Acids in Aqueous PEG-400
Chen, Ying,Hu, Min,Tang, Bo-Xiao,Wang, Yi-Hua,Wen, Qi-Qi,Xie, Bao-Xing,Yang, Shi-Yao,Zhong, Hai-Qing,Zou, Hong
supporting information, p. 793 - 796 (2020/05/19)
A novel and ligand-free method was developed for the decarboxylative cross-coupling of alkynylcarboxylic acids with arylboronic acids. By using an environmentally friendly H 2 O-poly(ethylene glycol) (PEG-400) system as the reaction medium, a series of internal alkynes were synthesized in good yields and with remarkable selectivity. The Pd(OAc) 2-H 2 O-PEG-400 catalytic system could be used for up to three cycles without any loss of activity, demonstrating the robustness of the approach.
Interfacing High-Energy Charge-Transfer States to a Near-IR Sensitizer for Efficient Electron Transfer upon Near-IR Irradiation
Alsaleh, Ajyal Z.,D'Souza, Francis,Misra, Rajneesh,Patil, Yuvraj,Pinjari, Dilip
supporting information, p. 23697 - 23705 (2020/12/01)
Push–pull systems comprising of triphenylamine–tetracyanobutadiene (TPA-TCBD), a high-energy charge-transfer species, are linked to a near-IR sensitizer, azaBODIPY, for promoting excited-state CS. These systems revealed panchromatic absorption owing to in
A Study of Polarization and Directing Effects of Unsymmetrical Alkynes Using Regioselective Pd-Catalyzed Bromoallylation
Topolov?an, Nikola,Hara, Shuto,Císa?ová, Ivana,To?ner, Zdeněk,Kotora, Martin
supporting information, p. 234 - 240 (2020/01/22)
Herein is disclosed the first comprehensive study of factors that affect the regioselectivity of PdBr2(PhCN)2-catalyzed bromoallylation of unsymmetrically substituted internal alkynes. The study was performed on a wide array of electronically and structurally diverse alkynes with aryl-aryl, aryl-ferrocenyl, and aryl-alkyl substitutions. The regioselective formation of bromoallylation products was mostly driven by the polarization of the triple bond in aryl-aryl and aryl-ferrocenyl-substituted ethynes. On the other hand, directing effect, which arises from the presence of a directing group in the side-chain of aryl-alkyl-substituted alkynes, was the dominating factor that determined the regioselectivity of these reactions.
