Article
Chemistry, Organic
Hai Lin, Shengzhang Liu, Qing Li, Qi Zhang, Lingyun Yang, Tao Wang, Jin Luo
Summary: This article describes a novel and efficient electrochemical oxidative transamidation of tertiary amines with N-acyl imides. The protocol is environmentally friendly and easy to handle, as tertiary amines are used as surrogates for secondary amines. The C-N bond of tertiary amines is cleaved, preparing amide compounds in a facile approach with 29 examples in yields ranging from 11% to 80%.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Isabel Abanades Lazaro, Ross S. Forgan, Francisco. G. Cirujano
Summary: The influence of composition and textural characteristics of ultra-small isoreticular UiO-type metal-organic frameworks (MOFs) on catalytic performance is evaluated in this study. The activity of Zr-MOF nanoparticles is tested using two different amide bond formation reactions as proof-of-concept. The results provide insights into the catalytic mechanism and optimal properties for enhancing performance.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Yujuan Wang, Yiyang Cheng, Lei Zhong, Shuhui Lei, Yun He, Yuanwei Dai
Summary: A highly efficient palladium-catalyzed glycosylation reaction between 3,4-O-carbonate glycals and acid-labile oximes is described. This method offers a broad substrate scope, high functional group tolerance, and easy scalability, resulting in glycosyl oximes with excellent yields, exclusive β-selectivity, and retention of Z/E geometries. The versatility of this approach is demonstrated through site-selective transformations and late-stage glycodiversification of bioactive molecules. Overall, this strategy provides an efficient toolkit for accessing valuable N-O-linked glycosides.
Article
Chemistry, Applied
Rebecca B. Watson, Todd W. Butler, Jacob C. DeForest
Summary: In this study, we demonstrate the application of Bronsted acid-activated N-acyl imidazoliums as versatile intermediates in carbonyl transformations, showing high efficiency and scalability. The method was successfully validated on a diverse set of compounds with up to 91% yield, including the synthesis of an electron-deficient carbamate on a multikilogram scale.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Chandra Shekhar Nishad, Krishna Kanta Haldar, Biplab Banerjee
Summary: A mild and efficient metal-free one-pot procedure for the synthesis of N-sulfonyl amidines via the direct reaction of sulfonamides with secondary amines without using any additives was reported. The reaction conditions tolerate a wide range of substrates with various functional groups. Preliminary mechanistic studies suggest that the secondary amine serves as both a C1 source of the amidine group and an aminating agent. The synthetic utility of this method was demonstrated in the late-stage functionalization of drug molecules at the gram scale.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuanyuan Ping, Xiao Li, Qi Pan, Wangqing Kong
Summary: Ligand-directed divergent synthesis is a strategy that can transform common starting materials into distinct molecular scaffolds. This strategy enables the rapid construction of structurally rich collection of small molecules for biological evaluation and reveals novel modes of catalytic transformation, representing one of the most sought-after challenges in synthetic chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zheng-Lin Yang, Xin-Liang Xu, Xue-Rong Chen, Zhi-Feng Mao, Yi-Feng Zhou
Summary: A silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was successfully achieved in this study, leading to the synthesis of a series of N-acylureas in moderate to good yields. This provides a new research direction for the application of dioxazolones and isocyanides in synthetic chemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yingwei Wang, Mingrong Yang, Chichou Lao, Zhihong Jiang
Summary: We report a new and simple method for the synthesis of dl-2,3-diamide-1,4-diones. This method is highly efficient and environmentally friendly. Experimental results suggest that the substrate undergoes autoxidation followed by diastereoselective SN2 reaction.
Article
Chemistry, Applied
Biao Zhang, Pan Zhou, Hui Xu, Jiuzhong Huang, Yulin Sun, Donghan Liu, Fuchao Yu
Summary: A copper(II)-mediated intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed, providing access to 5-acyl-3-furancarboxaldehydes with good yields and broad substrate scope. This reaction allows the formation of multiple new bonds through a radical cyclization process, showing potential application value in industry as demonstrated by gram-scale synthesis and application research.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Majid Ahmad Ganie, Faheem Fayaz, Muneer-ul-Shafi Bhat, Masood Ahmad Rizvi, Shabnam Raheem, Bhahwal Ali Shah
Summary: A mild approach for the synthesis of N-acyl-N,O-hemiacetals has been reported, utilizing an electron donor-acceptor complex. This protocol allows for direct access to electrophilic N-acylimines at room temperature without prefunctionalization of the hydroxyl group. The in situ generated N-acylimine reacts with different nucleophiles to yield diverse scaffolds.
Article
Chemistry, Inorganic & Nuclear
Hao Gao, Qianli Li, Ping Cui, Chen-Ho Tung, Lingbing Kong
Summary: Researchers have developed a facile route to synthesize B = C double-bonded systems, obtaining corresponding compounds through experiments and further analyzing their electronic structures through theoretical calculations and comparisons.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yiping Li, Jingyue Li, Guangjun Bao, Changjun Yu, Yuyang Liu, Zeyuan He, Peng Wang, Wen Ma, Junqiu Xie, Wangsheng Sun, Rui Wang
Summary: In this study, a novel coupling reagent NDTP was explored, which exhibited mild, nonirritating, convenient availability, and recyclability. It could activate carboxylic acids via acyl thiocyanide and enable the rapid synthesis of amides and peptides under mild conditions. Furthermore, the methodology was compatible with Fmoc-SPPS, providing an alternative approach for peptide manufacturing.
Article
Chemistry, Organic
Wenkuan Li, Sheng Zhang, Xiujuan Feng, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Summary: This study introduces a strategy for amide C-N bond activation using a ruthenium catalyst, where in situ formed bis-cycloruthenated complexes are demonstrated as key active species with superior oxidative addition ability. The direct C-H bond activation of 2-arylpyridines followed by amide C-N bond activation in the presence of a ruthenium precatalyst resulted in moderate to good yields of monoacylation products, with synthetically useful functional groups remaining intact during the tandem C-H/C-N bond activation reactions.
Article
Chemistry, Organic
Ramdas Sreedharan, Thirumanavelan Gandhi
Summary: alpha-Branched amines bearing beta-carbonyl in isoindolinones were synthesized via the aroylation of C(sp (3))-H carbon adjacent to the nitrogen atom. Unactivated tertiary amides and unactivated alkyl esters were used as electrophile sources. The reaction showed high functional group compatibility and could be applied to a range of substrates, including organometallic ferrocenyl esters and indole methyl esters with an acidic NH moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Robert D. Bradley, Ana Bahamonde
Summary: This paper describes a mild strategy to promote amide arylations by proposing photoinduced oxidation of a Ni(II) aryl amido intermediate to facilitate the challenging C-N reductive elimination step at moderate temperatures. The use of mildly basic conditions enables a broad scope of reactions, including protected amino acids, heterocycles, phenols, and sterically hindered substituents. Therefore, this work presents an attractive strategy to enable late-stage functionalization of pre-existing amide moieties in commercial drugs and natural products.
Article
Chemistry, Inorganic & Nuclear
John R. Coombs, Rebecca A. Green, Frederick Roberts, Eric M. Simmons, Jason M. Stevens, Steven R. Wisniewski
Article
Chemistry, Organic
Steven R. Wisniewski, Jason M. Stevens, Miao Yu, Kenneth J. Fraunhoffer, Evan O. Romero, Scott A. Savage
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Medicinal
Chunjian Liu, James Lin, Ryan Moslin, John S. Tokarski, Jodi Muckelbauer, ChiehYing Chang, Jeffrey Tredup, Dianlin Xie, Hyunsoo Park, Peng Li, Dauh-Rurng Wu, Joann Strnad, Adriana Zupa-Fernandez, Lihong Cheng, Charu Chaudhry, Jing Chen, Cliff Chen, Huadong Sun, Paul Elzinga, Celia D'arienzo, Kathleen Gillooly, Tracy L. Taylor, Kim W. McIntyre, Luisa Salter-Cid, Louis J. Lombardo, Percy H. Carter, Nelly Aranibar, James R. Burke, David S. Weinstein
ACS MEDICINAL CHEMISTRY LETTERS
(2019)
Article
Chemistry, Applied
Federico Lora Gonzalez, Steven R. Wisniewski, Kishta Katipally, Jason M. Stevens, Victor Rosso, Brendan Mack, Thomas M. Razler
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2019)
Article
Chemistry, Applied
Gregory L. Beutner, Benjamin M. Cohen, Albert J. DelMonte, Darryl D. Dixon, Kenneth J. Fraunhoffer, Andrew W. Glace, Ehrlic Lo, Jason M. Stevens, Dale Vanyo, Christopher Wilbert
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2019)
Article
Chemistry, Applied
Jun Qiu, Anisha Patel, Jason M. Stevens
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Physical
Anuji Abraham, Eric Chan, Hyunsoo Park
SOLID STATE NUCLEAR MAGNETIC RESONANCE
(2020)
Article
Chemistry, Applied
Jun Qiu, Jason M. Stevens
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Pharmacology & Pharmacy
Prashant Agarwal, Daniel G. Greene, Scott Sherman, Kaitlyn Wendl, Leonela Vega, Hyunsoo Park, Roman Shimanovich, Darren L. Reid
Summary: Sustained-release formulations are important for converting efficacious molecules into therapeutic products. Research on hydrogel-based drug delivery has focused on synthesizing new materials, but there is limited attention to factors like structural characterization and technology development. Commercially available thermosensitive hydrogel systems have shown potential for delaying drug release, with one system demonstrating higher complex viscosity and slower diffusivity compared to another.
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2021)
Article
Multidisciplinary Sciences
Benjamin J. Shields, Jason Stevens, Jun Li, Marvin Parasram, Farhan Damani, Jesus I. Martinez Alvarado, Jacob M. Janey, Ryan P. Adams, Abigail G. Doyle
Summary: Reaction optimization and parameter optimization are crucial in synthetic chemistry and artificial intelligence, respectively. Bayesian optimization algorithm has shown exceptional performance in tuning machine learning models and has been applied in chemistry. However, its application in reaction optimization in synthetic chemistry has not been explored. Adopting Bayesian optimization methods into everyday laboratory practices could lead to more efficient synthesis of functional chemicals.
Article
Chemistry, Applied
Jason M. Stevens, Eric M. Simmons, Yichen Tan, Alina Borovika, Junying Fan, Robert Forest, Peng Geng, Carlos A. Guerrero, Sha Lou, Dimitri Skliar, Sarah E. Steinhardt, Neil A. Strotman
Summary: This study describes the invention of a commercial route to the Bruton's tyrosine kinase inhibitor branebrutinib (BMS-986195) in four total chemical steps. By utilizing high-throughput experimentation and a first-principles approach, a novel indolization reaction that rapidly generated high synthetic complexity was identified as the centerpiece of the synthesis.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Inorganic & Nuclear
Jason M. Stevens, Jun Li, Eric M. Simmons, Steven R. Wisniewski, Stacey DiSomma, Kenneth J. Fraunhoffer, Peng Geng, Bo Hao, Erika W. Jackson
Summary: This study generated a large dataset to investigate the performance of catalysts and ligands in the aryl (pseudo)halide borylation reaction. It found that simple triarylphosphines and mixed aryl-alkyl phosphines performed well. Machine learning models were used to predict the reaction performance of ligands not included in the training set.
Article
Chemistry, Multidisciplinary
Jose Antonio Garrido Torres, Sii Hong Lau, Pranay Anchuri, Jason M. Stevens, Abigail G. Doyle, Jose E. Tabora, Jun Li, Alina Borovika, Ryan P. Adams
Summary: We developed an open-source experimental design platform based on Bayesian optimization algorithm for multiimentation (HTE) and virtual screening data sets. The platform optimized the reaction yield and enantioselectivity in a short time period, surpassing human-driven optimization. To make it more accessible to nonexperts, a graphical user interface with features like real-time condition modification and data visualization was developed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Victor W. Rosso, Zhiwei Yin, Heba Abourahma, Ariel Furman, Shasad Sharif, Andrew Werneth, Jason M. Stevens, Frederick Roberts, Darpandeep Aulakh, Roger Sommer, Amy A. Sarjeant
Summary: To quickly generate and identify crystalline solids for organic compounds, a rapid and adaptable crystallization screening strategy is needed. This study describes a system that utilizes a standard platform small-scale crystallizer screening array, automated polarized light microscope, and PXRD analysis instrument to deliver reliable and consistent results. Data science technologies are used to streamline data visualization and processing. The developed workflow successfully identifies multiple polymorphs of a test compound using single-crystal and PXRD analyses in a single screening experiment on 200 mg of input material.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
