Article
Chemistry, Physical
Ruchita R. Thakore, Balaram S. Takale, Vani Singhania, Fabrice Gallou, Bruce H. Lipshutz
Summary: The new technology enables efficient cyanation reactions of highly complex molecules in water, with significant implications for advancing drug synthesis and discovery.
Article
Chemistry, Organic
Fusheng Bie, Xuejing Liu, Han Cao, Yijun Shi, Tongliang Zhou, Michal Szostak, Chengwei Liu
Summary: The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.
Article
Chemistry, Organic
Mengna Liu, Benqiang Cui, Chuntao Zhong, Yanhui Shi, Yanfeng Dang, Changsheng Cao
Summary: A palladium-catalyzed cyanation of aryl dimethylsulfonium salts using K-4[Fe-(CN)(6)]center dot 3H(2)O as the cyanating reagent was successfully developed. The reaction proceeded under base-free conditions and yielded aryl nitriles with up to 92% yields. The protocol also allowed direct transformation of aryl sulfides to aryl nitriles, and the reaction mechanism was investigated using density functional theory calculations.
Article
Chemistry, Organic
Yanling Zhang, Zhiguo Zhang, Yuanyuan Hu, Yunkui Liu, Hongwei Jin, Bingwei Zhou
Summary: We have described a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides. Aryl/alkenyl iodines and bromides were found to be competent electrophiles that reacted with alkyl isocyanides to afford nitrile compounds in moderate to good yields. This protocol features broad functional group tolerance, simple reaction conditions, and gram-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Hunter J. Wood, Shirley Lin, Amy H. Roy MacArthur
Summary: This study investigates an unusually low-temperature tandem catalytic process for the amidation of aryl bromides. The aryl bromide is first converted to an aryl iodide via halogen exchange, and then transformed into the aryl amide. Optimized reaction conditions with a high yield of 82% for the conversion of 4-bromotoluene to 4-(N-methylphenyl)-benzamide were identified.
Article
Chemistry, Organic
Kartic Manna, Ranjan Jana
Summary: We describe a mild and highly selective palladium-catalyzed cross-electrophile coupling between aromatic diazonium salts and aryl iodides or diaryliodonium salts in a water-ethanol (2:1) medium. Mechanistic studies revealed the importance of ethanol in generating an active Pd(0) catalyst, and the counterion of the diazonium salt promotes the formation of a cationic Pd(II) species that facilitates subsequent oxidative addition to aryl iodides/diaryliodonium salts. The presence of silver(I) salt is crucial for maintaining the catalytic activity of palladium by removing iodide ions as precipitates.
Article
Chemistry, Organic
Xuan-Di Song, Meng-Meng Guo, Shuang Xu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed, allowing for efficient stereocontrolled synthesis of a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance. The one-pot reaction is simple to operate, providing a convenient method for the synthesis of complex molecules.
Article
Chemistry, Organic
Xinmiao Huang, Ling Tang, Zhiyong Song, Shuangshuang Jiang, Xianmao Liu, Ming Ma, Bo Chen, Yuanhong Ma
Summary: A nickel catalysis system has been developed for the desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with aryl bromides to form diverse biaryl compounds. The isolated and confirmed Ar-Ni(II)-SO(2)CF3 complex with a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species provides solid evidence for understanding the C(Ar)-SO2 bond activation and reaction mechanism.
Review
Chemistry, Multidisciplinary
Meng-Yu Xu, Bin Xiao
Summary: Palladium-catalyzed cross-coupling reactions play a crucial role in the complex synthetic field. Our research group focuses on developing new germanium-based reagents and catalytic processes. Over the past three years, we have established new methods for the synthesis of novel compounds, with particular emphasis on the unique properties of alkyl carbagermatranes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yinpeng Wang, Mingming Zhao, Jingke Peng, Hongxia Zheng, Heng-Ying Xiong, Guangwu Zhang
Summary: The first Pd(0)-catalyzed synthesis of aryl-methylene ethers from hydrobenzoxazoles (hydrothiazoles) using dichloromethane (DCM) as the C1 feedstock is reported. This protocol demonstrates a broad substrate scope (38 examples) and wide tolerance to functional groups. The aryl-methylene ether adducts have been successfully coupled with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM serves as a twofold electrophile, undergoing double C-Cl bond cleavage to react with hydrobenzoxazoles.
Article
Chemistry, Multidisciplinary
Gianluigi Albano, Gianfranco Decandia, Maria Annunziata M. Capozzi, Nicola Zappimbulso, Angela Punzi, Gianluca M. Farinola
Summary: The study found that IR irradiation-assisted solvent-free Pd-catalyzed direct C-H bond arylation of (hetero)arenes was achieved, tolerating many functional groups and making an important contribution to the development of protocols fitting with the principles of green chemistry.
Article
Chemistry, Organic
Jing-Ao Ren, Jin-He Na, Chao Gui, Chengping Miao, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A nickel-catalyzed direct cross-coupling between unactivated aryl fluorides and aryl bromides was achieved. This one-pot reaction proceeds effectively at room temperature in THF, avoiding the use of preformed and sensitive organometallic reagents. The desired biaryls are produced in modest to good yields via C-F bond cleavage in the presence of a phosphine ligand and magnesium powder (with or without TMSCl).
Article
Chemistry, Organic
Yiming You, Jiawen Hu, Tao Wu
Summary: Few studies have been conducted on aryl-substituted allenyl monofluorides due to concerns about their stability. In this study, we report a copper-catalyzed regioselective synthesis of these structures using inexpensive and accessible aryl boronic esters under mild conditions. The arylated allenyl monofluorides were stable enough to be isolated and easily converted to various other fluorine-containing compounds. Preliminary asymmetric attempts indicated that the reaction could proceed via a selective beta-fluorine elimination process.
Article
Chemistry, Organic
Tristan Delcaillau, Adrian Woenckhaus-Alvarez, Bill Morandi
Summary: A nickel-catalyzed cyanation method using Zn(CN)(2) as the cyanide source has been developed for the functionalization of aryl thioethers, involving both C-S bond activation and C-C bond formation. The combination of ligand dcype and base KOAc is crucial for the efficiency of this transformation. The scalability, low catalyst and reagent loadings, and high functional group tolerance make this reaction useful for late-stage derivatization and polymer recycling in organic chemistry.
Article
Chemistry, Multidisciplinary
Ryota Isshiki, Miki B. Kurosawa, Kei Muto, Junichiro Yamaguchi
Summary: A Ni-catalyzed aryl sulfide synthesis method was developed using 2-pyridyl sulfide as the sulfide donor, eliminating the need for odorous and toxic thiols. The Ni/dcypt catalyst played a crucial role in the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, with mechanistic studies showing its ability to undergo oxidative additions and ligand exchanges simultaneously.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Martin D. Johnson, Scott A. May, Brian Haeberle, Gordon R. Lambertus, Shon R Pulley, James R. Stout
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2016)
Article
Chemistry, Applied
Sergey V. Tsukanov, Martin D. Johnson, Scott A. May, Morgan Rosemeyer, Michael A. Watkins, Stanley P. Kolis, Matthew H. Yates, Jeffiey N. Johnston
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2016)
Article
Chemistry, Physical
Damian M. Grainger, Antonio Zanotti-Gerosa, Kevin P. Cole, David Mitchell, Scott A. May, Patrick M. Pollock, Joel R. Calvin
Article
Chemistry, Organic
Joel R. Calvin, Michael O. Frederick, Dana L. T. Laird, Jacob R. Remacle, Scott A. May
Article
Chemistry, Applied
Scott A. May, Martin D. Johnson, Timothy M. Braden, Joel R. Calvin, Brian D. Haeberle, Amy R. Jines, Richard D. Miller, Edward F. Plocharczyk, Gregory A. Rener, Rachel N. Richey, Christopher R. Schmid, Radhe K. Vaid, Hannah Yu
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2012)
Article
Chemistry, Applied
Martin D. Johnson, Scott A. May, Joel R. Calvin, Jacob Remacle, James R. Stout, William D. Diseroad, Nikolay Zaborenko, Brian D. Haeberle, Wei-Ming Sun, Michael T. Miller, John Brennan
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2012)
Article
Chemistry, Applied
Alison N. Campbell, Kevin P. Cole, Joseph R. Martinelli, Scott A. May, David Mitchell, Patrick M. Pollock, Kevin A. Sullivan
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2013)
Article
Chemistry, Organic
Radhe K. Vaid, Jeremy T. Spitler, Sathish Boini, Scott A. May, Richard C. Hoying
SYNTHESIS-STUTTGART
(2012)
Article
Chemistry, Organic
Radhe K. Vaid, Sathish Boini, Jeremy T. Spitler, Yangwei John Pu, Scott A. May, Hannah Yu, Wu Sizhong, Jie Fu, Guoliang Zhang
SYNTHESIS-STUTTGART
(2013)
Article
Chemistry, Organic
Hannah Yu, Rachel N. Richey, Javier Mendiola, Marta Adeva, Carmen Somoza, Scott A. May, Matthew W. Carson, Michael J. Coghlan
TETRAHEDRON LETTERS
(2008)
Article
Chemistry, Organic
SA May, TM Wilson, AL Fields
TETRAHEDRON LETTERS
(2006)
Article
Chemistry, Medicinal
OB Wallace, KS Lauwers, JA Dodge, SA May, JR Calvin, R Hinklin, HU Bryant, PK Shetler, MD Adrian, AG Geiser, M Sato, TP Burris
JOURNAL OF MEDICINAL CHEMISTRY
(2006)
