Article
Chemistry, Applied
Lilian Geniller, Marc Taillefer, Florian Jaroschik, Alexis Prieto
Summary: The Ni-photoredox catalyzed desulfurative cross-coupling reaction enables the synthesis of various unsymmetrical diarylmethane molecules under mild reaction conditions, providing new transformations of abundant, naturally occurring thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Suvam Paul, Sourav Das, Tathagata Choudhuri, Papiya Sikdar, Avik Kumar Bagdi
Summary: A visible light-induced cross-dehydrogenative methodology has been developed for the regioselective sulfenylation of pyrazolo[1,5-a]pyrimidine derivatives. This protocol allows the synthesis of a library of 3-(aryl/heteroaryl thio)pyrazolo[1,5-a]pyrimidine derivatives with broad functionalities. The methodology also shows selectivity, scalability, and efficiency in sulfenylation of various substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Suvam Paul, Sourav Das, Tathagata Choudhuri, Papiya Sikdar, Avik Kumar Bagdi
Summary: A visible-light-induced cross-dehydrogenative methodology has been developed for the regioselective sulfenylation of pyrazolo[1,5-a]pyrimidine derivatives. Rose bengal, blue LEDs, KI, K2S2O8, and DMSO are all essential for this photocatalytic transformation. The protocol is applicable for the synthesis of a library of 3-(aryl/heteroaryl thio)pyrazolo[1,5-a]pyrimidine derivatives with broad functionalities. The selectivity and scalability of the methodology have been also demonstrated. Moreover, the efficiency of this strategy for sulfenylation of pyrazoles, indole, imidazoheterocycles, and 4-hydroxy coumarin has been proven. The mechanistic investigation revealed the radical-based mechanism and formation of diaryl disulfide as a key intermediate for this cross-dehydrogenative coupling reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Guozhe Guo, Yong Yuan, Shuocheng Wan, Xuehui Cao, Yali Sun, Congde Huo
Summary: This study demonstrated for the first time that K2S2O8 promoted dehydrative cross-coupling reaction can synthesize a wide range of allyl sulfides, with broad substrate scopes and tolerance to various substrates, possibly involving a radical addition process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yangzhong Qin, Rui Sun, Nikolas P. Gianoulis, Daniel G. Nocera
Summary: The researchers conducted a comprehensive mechanistic study of photoredox nickel-catalyzed C-S cross-coupling, revealing a self-sustained productive Ni(I/III) cycle, the role of in situ formed pyridinium iodide as a dominant quencher, and critical intermediates in the reaction pathway. These mechanistic insights not only provided a complete reaction cycle but also allowed for optimization of reaction efficiency and broadening the substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Zi-Chao Wang, Jia-Wen Zhang, Ming Joo Koh, Shi-Liang Shi
Summary: In this study, a highly selective carbonickelation of light alkenes was reported, enabling efficient synthesis of diverse compounds through addition reactions with various reagents. The use of bulky N-heterocyclic carbene ligands played a crucial role in the reaction. This strategy provides a rare, modular platform for upgrading feedstock alkenes and is expected to find broad applications in medicinal chemistry and industrial processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Alec H. Christian
Summary: The metallaphotoredox-catalyzed C-S cross-coupling allows for the formation of biaryl thioethers from heteroaryl bromides and alpha-thioacetic acids. This method facilitates cross-coupling between building blocks containing reactive functional groups, nitrogen heterocycles, and pharmaceutically relevant scaffolds. Mechanistic experiments show a unique pathway for the C-S cross-coupling to occur.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Guodong Li, Ke Yu, Jiajun Yang, Bo Xu, Qianjin Chen
Summary: An electrochemical radical strategy involving alkene substrates provides a powerful approach for alkene functionalization. The reaction described in the study enables the synthesis of gem-bisarylthio enamines with good functional group tolerance and high yields, without the need for additional oxidants, transition-metal catalysts, or bases, and can be easily scaled up for gram-scale production.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Linlin Ding, Yue Zhao, Hongjian Lu, Zhuangzhi Shi, Minyan Wang
Summary: For the first time, a catalytic enantioselective propargyl-aryl cross-coupling between two electrophiles was achieved in a stereoconvergent manner. The potential utility of this conversion is demonstrated in the facile construction of stereoenriched bioactive molecule derivatives and medicinal compounds based on the diversity of acetylenic chemistry. Detailed experimental studies have revealed the key mechanistic features of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chao-Peng Zhang, Tian-Zhang Wang, Yu-Feng Liang
Summary: This study reports a reductive cross-coupling reaction using manganese as a catalyst, which efficiently converts disulfides into thioethers. The advantages of this method include low cost and environmental friendliness, as well as broad substrate scope and simple reaction conditions. Therefore, this method has important application prospects.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xi He, Weili Song, Xuemin Liu, Jiamin Huang, Ruilong Feng, Shaodong Zhou, Jianquan Hong, Xin Ge
Summary: A sustainable and general multicomponent cross-coupling method for the synthesis of 3-chalcogenylindoles from indoles using aryl iodides and elemental sulfur under aqueous micellar conditions is developed. Elemental sulfur serves as an eco-friendly and easy-handling sulfur source, generating thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM stabilizes thiyl radicals, enabling C-S coupling with readily available indoles through single-electron transfer. The aqueous micellar system can be recycled and reused with good yields and can also be extended to the conversion of elemental selenium.
Article
Chemistry, Applied
Masami Kuriyama, Genki Maeda, Kazuya Kamata, Yusuke Kodama, Kosuke Yamamoto, Osamu Onomura
Summary: The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was achieved using a 1,10-phenanthroline-type ligand. Functionalized and heterocycle-containing boroxines were suitable partners for this reaction, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was successfully accomplished. Moreover, the gram-scale reaction proceeded smoothly with a high yield of desired product.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jinglin An, Xue Zhou, Yifan Zhang, Zhenfei Ye, Qianyou Guo, Hao Song, Zhenlei Song, Xiao-Yu Liu, Yong Qin
Summary: A nickel-catalysed reductive cross-coupling reaction was developed to synthesize all-carbon tetrasubstituted cycloalkenes in moderate to excellent yields up to 92%. Mechanistic studies revealed the significant assisting role of the carboxylic acid group in this sterically demanding coupling reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biology
Melody G. Campbell, David Veesler, Anchi Cheng, Clinton S. Potter, Bridget Carragher
Article
Chemistry, Multidisciplinary
Zhe Zhang, Angel Puente, Fang Wang, Martin Rahm, Yuncai Mei, Herbert Mayr, G. K. Surya Prakash
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Multidisciplinary Sciences
Henriette E. Autzen, Alexander G. Myasnikov, Melody G. Campbell, Daniel Asarnow, David Julius, Yifan Cheng
Article
Multidisciplinary Sciences
Xiaodi Yu, David Veesler, Melody G. Campbell, Mary E. Barry, Francisco J. Asturias, Michael A. Barry, Vijay S. Reddy
Article
Biochemistry & Molecular Biology
Young Kim, Zhe Zhang, Jae-Hyuck Shim, Tae Sup Lee, Ching-Hsuan Tung
BIOORGANIC & MEDICINAL CHEMISTRY
(2018)
Article
Microbiology
Jennifer M. Binning, Amber M. Smith, Judd F. Hultquist, Charles S. Craik, Nathalie Caretta Cartozo, Melody G. Campbell, Lily Burton, Florencia La Greca, Michael J. McGregor, Hai M. Ta, Koen Bartholomeeusen, B. Matija Peterlin, Nevan J. Krogan, Natalia Sevillano, Yifan Cheng, John D. Gross
Article
Biochemistry & Molecular Biology
Anthony Cormier, Melody G. Campbell, Saburo Ito, Shenping Wu, Jianlong Lou, James Marks, Jody L. Baron, Stephen L. Nishimura, Yifan Cheng
NATURE STRUCTURAL & MOLECULAR BIOLOGY
(2018)
Article
Biochemistry & Molecular Biology
Caitlin I. Stoddard, Suhua Feng, Melody G. Campbell, Wanlu Liu, Haifeng Wang, Xuehua Zhong, Yana Bernatavichute, Yifan Cheng, Steven E. Jacobsen, Geeta J. Narlikar
Article
Multidisciplinary Sciences
Laura E. Rosen, Joseph E. Klebba, Jonathan B. Asfaha, Chloe M. Ghent, Melody G. Campbell, Yifan Cheng, David O. Morgan
NATURE COMMUNICATIONS
(2019)
Article
Biochemistry & Molecular Biology
Melody G. Campbell, Anthony Cormier, Saburo Ito, Robert Seed, Andrew J. Bondesson, Jianlong Lou, James D. Marks, Jody L. Baron, Yifan Cheng, Stephen L. Nishimura
Article
Biochemistry & Molecular Biology
Feng Wang, Zanlin Yu, Miguel Betegon, Melody G. Campbell, Tural Aksel, Jianhua Zhao, Sam Li, Shawn M. Douglas, Yifan Cheng, David A. Agard
JOURNAL OF STRUCTURAL BIOLOGY
(2020)
Article
Multidisciplinary Sciences
David E. Gordon, Joseph Hiatt, Mehdi Bouhaddou, Veronica V. Rezelj, Svenja Ulferts, Hannes Braberg, Alexander S. Jureka, Kirsten Obernier, Jeffrey Z. Guo, Jyoti Batra, Robyn M. Kaake, Andrew R. Weckstein, Tristan W. Owens, Meghna Gupta, Sergei Pourmal, Erron W. Titus, Merve Cakir, Margaret Soucheray, Michael McGregor, Zeynep Cakir, Gwendolyn Jang, Matthew J. O'Meara, Tia A. Tummino, Ziyang Zhang, Helene Foussard, Ajda Rojc, Yuan Zhou, Dmitry Kuchenov, Ruth Huttenhain, Jiewei Xu, Manon Eckhardt, Danielle L. Swaney, Jacqueline M. Fabius, Manisha Ummadi, Beril Tutuncuoglu, Ujjwal Rathore, Maya Modak, Paige Haas, Kelsey M. Haas, Zun Zar Chi Naing, Ernst H. Pulido, Ying Shi, Inigo Barrio-Hernandez, Danish Memon, Eirini Petsalaki, Alistair Dunham, Miguel Correa Marrero, David Burke, Cassandra Koh, Thomas Vallet, Jesus A. Silvas, Caleigh M. Azumaya, Christian Billesbolle, Axel F. Brilot, Melody G. Campbell, Amy Diallo, Miles Sasha Dickinson, Devan Diwanji, Nadia Herrera, Nick Hoppe, Huong T. Kratochvil, Yanxin Liu, Gregory E. Merz, Michelle Moritz, Henry C. Nguyen, Carlos Nowotny, Cristina Puchades, Alexandrea N. Rizo, Ursula Schulze-Gahmen, Amber M. Smith, Ming Sun, Iris D. Young, Jianhua Zhao, Daniel Asarnow, Justin Biel, Alisa Bowen, Julian R. Braxton, Jen Chen, Cynthia M. Chio, Un Seng Chio, Ishan Deshpande, Loan Doan, Bryan Faust, Sebastian Flores, Mingliang Jin, Kate Kim, Victor L. Lam, Fei Li, Junrui Li, Yen-Li Li, Yang Li, Xi Liu, Megan Lo, Kyle E. Lopez, Arthur A. Melo, Frank R. Moss, Phuong Nguyen, Joana Paulino, Komal Ishwar Pawar, Jessica K. Peters, Thomas H. Pospiech, Maliheh Safari, Smriti Sangwan, Kaitlin Schaefer, Paul Thomas, Aye C. Thwin, Raphael Trenker, Eric Tse, Tsz Kin Martin Tsui, Feng Wang, Natalie Whitis, Zanlin Yu, Kaihua Zhang, Yang Zhang, Fengbo Zhou, Daniel Saltzberg, Anthony J. Hodder, Amber S. Shun-Shion, Daniel M. Williams, Kris M. White, Romel Rosales, Thomas Kehrer, Lisa Miorin, Elena Moreno, Arvind H. Patel, Suzannah Rihn, Mir M. Khalid, Albert Vallejo-Gracia, Parinaz Fozouni, Camille R. Simoneau, Theodore L. Roth, David Wu, Mohd Anisul Karim, Maya Ghoussaini, Ian Dunham, Francesco Berardi, Sebastian Weigang, Maxime Chazal, Jisoo Park, James Logue, Marisa McGrath, Stuart Weston, Robert Haupt, C. James Hastie, Matthew Elliott, Fiona Brown, Kerry A. Burness, Elaine Reid, Mark Dorward, Clare Johnson, Stuart G. Wilkinson, Anna Geyer, Daniel M. Giesel, Carla Baillie, Samantha Raggett, Hannah Leech, Rachel Toth, Nicola Goodman, Kathleen C. Keough, Abigail L. Lind, Reyna J. Klesh, Kafi R. Hemphill, Jared Carlson-Stevermer, Jennifer Oki, Kevin Holden, Travis Maures, Katherine S. Pollard, Andrej Sali, David A. Agard, Yifan Cheng, James S. Fraser, Adam Frost, Natalia Jura, Tanja Kortemme, Aashish Manglik, Daniel R. Southworth, Robert M. Stroud, Dario R. Alessi, Paul Davies, Matthew B. Frieman, Trey Ideker, Carmen Abate, Nolwenn Jouvenet, Georg Kochs, Brian Shoichet, Melanie Ott, Massimo Palmarini, Kevan M. Shokat, Adolfo Garcia-Sastre, Jeremy A. Rassen, Robert Grosse, Oren S. Rosenberg, Kliment A. Verba, Christopher F. Basler, Marco Vignuzzi, Andrew A. Peden, Pedro Beltrao, Nevan J. Krogan
Article
Multidisciplinary Sciences
Michael Schoof, Bryan Faust, Reuben A. Saunders, Smriti Sangwan, Veronica Rezelj, Nick Hoppe, Morgane Boone, Christian B. Billesbolle, Cristina Puchades, Caleigh M. Azumaya, Huong T. Kratochvil, Marcell Zimanyi, Ishan Deshpande, Jiahao Liang, Sasha Dickinson, Henry C. Nguyen, Cynthia M. Chio, Gregory E. Merz, Michael C. Thompson, Devan Diwanji, Kaitlin Schaefer, Aditya A. Anand, Niv Dobzinski, Beth Shoshana Zha, Camille R. Simoneau, Kristoffer Leon, Kris M. White, Un Seng Chio, Meghna Gupta, Mingliang Jin, Fei Li, Yanxin Liu, Kaihua Zhang, David Bulkley, Ming Sun, Amber M. Smith, Alexandrea N. Rizo, Frank Moss, Axel F. Brilot, Sergei Pourmal, Raphael Trenker, Thomas Pospiech, Sayan Gupta, Benjamin Barsi-Rhyne, Vladislav Belyy, Andrew W. Barile-Hill, Silke Nock, Yuwei Liu, Nevan J. Krogan, Corie Y. Ralston, Danielle L. Swaney, Adolfo Garcia-Sastre, Melanie Ott, Marco Vignuzzi, Peter Walter, Aashish Manglik
Article
Medicine, Research & Experimental
Naoki Takasaka, Robert I. Seed, Anthony Cormier, Andrew J. Bondesson, Jianlong Lou, Ahmed Elattma, Saburo Ito, Haruhiko Yanagisawa, Mitsuo Hashimoto, Royce Ma, Michelle D. Levine, Jean Publicover, Rashaun Potts, Jillian M. Jespersen, Melody G. Campbell, Fraser Conrad, James D. Marks, Yifan Cheng, Jody L. Baron, Stephen L. Nishimura
Article
Chemistry, Multidisciplinary
Weiqi Zhang, Zhe Zhang, Ching-Hsuan Tung
CHEMICAL COMMUNICATIONS
(2017)