Article
Chemistry, Multidisciplinary
Pierre Hansjacob, Frederic R. Leroux, Vincent Gandon, Morgan Donnard
Summary: The palladium-catalyzed silylcyanation of ynamides is highly selective, producing exclusively tetrasubstituted 2-aminoacrylonitriles derivatives. The stereoselectivity is directly controlled by the nature of the substituent at the beta-position of the ynamide. The reaction is tolerant of various functional groups and provides a general method to access fully substituted 2-aminoacrylonitriles. The mechanism of this intriguing transformation is elucidated by computational study, and the range of 2-aminoacrylonitriles is expanded through postfunctionalization using the newly installed vinylsilane functionality.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Rajeshwer Vanjari, Shubham Dutta, Shengwen Yang, Vincent Gandon, Akhila K. Sahoo
Summary: A cationic palladium-catalyzed arylalkenylation of ynamides was developed. The regioselective carbopalladation of the ynamide to form a vinylpalladium species was likely dictated by the putative keteniminium arylpalladium intermediate. The capture of this complex by the olefin generated linear conjugated beta-alkenyl aminodienes (especially with trans selectivity). The transformation exhibited a broad scope, tolerated labile functional groups, and produced 42 unusual molecular scaffolds with structural diversity. DFT studies provided valuable insights into the reaction mechanism.
Article
Chemistry, Multidisciplinary
Shashank Shandilya, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: Ynamide, a unique species with inherited polarization of nitrogen lone pair electron to triple bond, has been widely used for the development of novel synthetic methods and the construction of unusual N-bearing heterocycles. This review provides an overall scenic view into the gold catalyzed transformation of ynamides, including their reactivity towards various transfer reagents and carbon nucleophiles.
Article
Chemistry, Organic
Yanru Wang, Zhen Zhao, Songkui Lv, Lixia Ding, Xiao-Na Wang, Junbiao Chang
Summary: The metal-free catalytic regioselective hydroamination of ynamides with primary and secondary amines has been achieved using TfOH as the catalyst under mild reaction conditions, providing N-arylimines and ethene-1,1-diamines in good to excellent yields with wide functional group tolerance. Additionally, their applications in 2-aminoindole syntheses have been demonstrated.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xiao-Di Nie, Xiao-Li Han, Jian-Ting Sun, Chang-Mei Si, Bang-Guo Wei, Guo-Qiang Lin
Summary: This study introduces a novel method for the Ni(OTf)(2)-catalyzed hydroamination of ynamides with secondary amines, demonstrating high yields and excellent regioselectivity. The protocol shows good functional group tolerance for ynamides and a broad substrate scope of secondary aryl amines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ban Wang, Gavin E. Mccabe, Mitchell J. Parrish, Jujhar Singh, Matthias Zeller, Yongming Deng
Summary: A photoinduced selective hydroamination reaction of ynamides with nitrogen heteroaromatic nucleophiles has been developed using an organocatalytic photoredox system. This method allows for the direct construction of a diverse range of (Z)-alpha-azole enamides from ynamides and pyrazoles, triazoles, benzotriazoles, indazoles, and tetrazoles, providing a photocatalytic synthetic route to heterocyclic motifs commonly found in medicinal agents.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Paz Yepes, Angel L. Suarez-Sobrino, Miguel A. Rodriguez, Alfredo Ballesteros
Summary: The regio- and stereoselective carbosilylation reaction of tosylynamides with allylic trimethylsilanes is efficiently catalyzed by TMSNTf2 or HNTf2, resulting in high yields of (Z)-α-allyl-P-trimethylsilylenamides. Theoretical calculations reveal that the C-C triple bond of the ynamides is activated by the trimethylsilylium ion, leading to the formation of a P-trimethylsilylketenimonium cation. The subsequent transformations of the products demonstrate the synthetic utility of this reaction.
Article
Chemistry, Organic
Yuanjiu Xiao, Lei Tang, Tong-Tong Xu, Jian-Jun Feng
Summary: An atom-economical protocol for the efficient and highly selective trans-hydroarylation of ynamides with hydroxyarenes has been developed using B(C6F5)3 as the catalyst. This approach offers the advantages of readily available starting materials, low catalyst loading, mild reaction conditions, a broad substrate scope, ease of scale-up, and versatile functionalizations of the enamide products.
Article
Chemistry, Organic
Zenghui Sun, Xinhang Zhang, Jiayue Fu, Lianjie Zhang, Maosheng Cheng, Lu Yang, Yongxiang Liu
Summary: In this study, six 8-oxoprotoberberines were synthesized collectively in four steps with acceptable yields (14-19%), including 8-oxopalmatine, 8-oxopseudopalmatine, 8-oxoberberine, and 8-oxopseudoberberine. The synthetic route involved In-(OTf)(3)-catalyzed cyclization and Heck coupling. Additionally, the syntheses of natural products berberine, canadine, and iambertine were achieved via reductions of 8-oxoberberine, providing a concise approach to the synthesis of these alkaloids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Stephane Golling, Pierre Hansjacob, Nassim Bami, Frederic R. Leroux, Morgan Donnard
Summary: This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lucas Pages, Maxime Bouquin, Florian Jaroschik, Florian Monnier, Marc Taillefer
Summary: We present a simple protocol for the copper-catalyzed hydrothiolation of N-unsaturated precursors, enabling the room-temperature transformation of thiols into various thioethers and thioaminals with good selectivity. The use of a low loading of commercially available Cu(CH3CN)(4)PF6 catalyst facilitates the process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Philip J. Smith, Zixuan Tong, Julia Ragus, Pearse Solon, Kirk W. Shimkin, Edward A. Anderson
Summary: In this study, we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, achieving the formation of highly selective 7-aminoindolines by controlling the electronic properties of the alkyne partner. We also developed a complementary synthesis of bicyclic 1,2-dianiline derivatives by cyclotrimerization of yndiamides with terminal diynes.
Article
Chemistry, Organic
Jun-Qi Zhang, Chunjiao Shen, Shihao Shuai, Ling Fang, Dandan Hu, Jiali Wang, Yu Zhou, Bukuo Ni, Hongjun Ren
Summary: A green and efficient approach for the difunctionalization of ynamides by merging the electrochemical and organoseleniumcatalyzed processes is described. This strategy features mild reaction conditions, broad functional group tolerance and high atom-economy, and requires no external chemical oxidant, providing a sustainable alternative for the synthesis of polysubstituted oxazoles.
Article
Chemistry, Multidisciplinary
Aankhi Khamrai, Venkataraman Ganesh
Summary: This study demonstrates the potential of a bench-stable Ni0 complex, Ni(COD)(DQ), as a catalyst for the reductive coupling of aldehydes with alkynes and ynamides, providing silylated allyl alcohols with excellent yields and regioselectivities. Mass spectrometric identification of the intermediates and DFT studies supported the proposed mechanism.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Zhuo Chen, Xiao-Di Nie, Jian-Ting Sun, Ai-Mei Yang, Bang-Guo Wei
Summary: The Zn(OTf)(2)-catalyzed hydroamination of ynamides with aromatic amines has been developed, allowing for the synthesis of various substituted amidine compounds with moderate to excellent yields and high regioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Somnath Narayan Karad, Heena Panchal, Christopher Clarke, William Lewis, Hon Wai Lam
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Correction
Chemistry, Multidisciplinary
Johnathon D. Dooley, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Alistair Groves, Jose I. Martinez, Joshua J. Smith, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Simone M. Gillbard, Chieh-Hsu Chung, Somnath Narayan Karad, Heena Panchal, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
Correction
Chemistry, Multidisciplinary
Alistair Groves, Jose I. Martinez, Joshua J. Smith, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: This study describes a novel domino reaction involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization onto acyclic ketones to yield chiral tertiary-alcohol-containing products with high enantioselectivities. The reversible E/Z isomerization of the alkenylnickel intermediates allows overall anti-arylmetallative cyclization to occur, producing products with ring systems similar to certain diarylindolizidine alkaloids.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Simone M. Gillbard, Hon Wai Lam
Summary: The use of arylboron reagents in metal-catalyzed domino addition-cyclization reactions is an important synthetic strategy for the preparation of diverse, highly functionalized carbo- and heterocyclic products. Recent studies have shown that nickel catalysts offer unique reactivity and access to products that are otherwise difficult to obtain.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Luke O'Brien, Stephen P. Argent, Kristaps Ermanis, Hon Wai Lam
Summary: Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates were studied. The reactions showed high selectivity and provided a variety of functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Experimental evidence and density functional theory calculations revealed the mechanistic insights.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Dmitry Gorbachev, Elliot Smith, Stephen P. Argent, Graham N. Newton, Hon Wai Lam
Summary: This study describes the synthesis of new morphinan opioids by adding photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring. By using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the feasibility of late-stage modification of complex, highly functionalized substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Simone M. Gillbard, Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are discussed in this study.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Alistair Groves, Jinwei Sun, Hal R. I. Parke, Michael Callingham, Stephen P. Argent, Laurence J. Taylor, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Riccardo Di Sanza, Thi Le Nhon Nguyen, Naeem Iqbal, Stephen P. Argent, William Lewis, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Luke O'Brien, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Rebecca E. Ruscoe, Michael Callingham, Joshua A. Baker, Stamatis E. Korkis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Heena Panchal, Christopher Clarke, Charles Bell, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
