Article
Chemistry, Multidisciplinary
Ryo Tanaka, Yuki Hirata, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: This study reports a C-H bond addition reaction of 2-phenylpyridine derivatives with alpha,beta-unsaturated carboxylic acids catalyzed by Cp*Rh(iii)/BH3 center dot SMe2. The activation of C-H bonds with the rhodium catalyst and activation of alpha,beta-unsaturated carboxylic acids with the boron catalyst cooperatively work, and a BINOL-urea hybrid ligand significantly improved the reactivity. With the optimized hybrid catalytic system, various beta-disubstituted carboxylic acids were obtained under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ya-Mei Dai, Min Liu, Qin-Qiong Zeng, Xiaoting Li, Bi-Qin Wang, Ping Hu, Ke-Qing Zhao, Feijie Song, Zhang-Jie Shi
Summary: This study unveiled a skeleton reorganization of alkene-tethered benzocyclobutenols through Rh-catalyzed C-C bond cleavage coupled with intra- and intermolecular hydrogen transfer, leading to the synthesis of divergent benzofurans bearing 4-beta-hydroxy or 4-beta-keto moieties under pH- and redox-neutral conditions. The reaction pathway was finely tuned by the catalytic systems.
Article
Chemistry, Organic
Wenwei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing-Yuan Ge, Ningning Lv, Jiuxi Chen
Summary: We report a novel pathway to synthesize gamma-lactams using acetonitrile analogues as coupling partners. This method does not require oxidants, ligands, and Lewis acids, and exhibits a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Organic
Zhongxue Fang, Yu Wang, Yiming Ma, Xinyue Han, Zhaohong Liu, Yongquan Ning
Summary: This study presents the development of the Rh-catalyzed[2,3]-sigmatropic rearrangement of alkynyl carbenes with allyl sulfides. The protocol shows good tolerance towards various functional groups and enables the synthesis of valuable sulfide-substituted 1,5-enyne products. It is the first example of [2,3]-sigmatropic rearrangement of alkynyl carbenes. DFT analysis confirms the involvement of rhodium carbene generation, sulfoniumylides formation, and [2,3]-sigmatropic rearrangement pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Grace E. Hubbell, Jetze J. Tepe
Summary: This study reports a Rh(III)-catalyzed C-H activation/annulation using an imidazolone as an alkene partner to access dihydroisoquinolone-fused imidazolin-2-ones. These compounds resemble the scaffolds found in the pyrrole alkaloid family of natural products. The method allows for the construction of various urea-fused dihydroisoquinolone scaffolds, including heterocyclic moieties.
Article
Chemistry, Organic
Shao-Yong Chen, Yi-Chuan Zheng, Xu-Ge Liu, Jia-Lin Song, Lin Xiao, Shang-Shi Zhang
Summary: The indole-substituted trifluoromethyl sulfonium ylide was synthesized via the Cp*Rh(III)-catalyzed addition of diazocarbenoid to trifluoromethylthioether, and it represents the first example of an Rh(III)-catalyzed diazo-carbenoid addition reaction with trifluoromethylthioether. Several types of indole-substituted trifluoromethyl sulfonium ylide were prepared using mild reaction conditions. The method demonstrated high compatibility with functional groups and a wide substrate scope. Furthermore, it was found to be complementary to the method previously disclosed using a Rh(II) catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
David L. Davies, Kuldip Singh, Neringa Tamosiunaite
Summary: The acetate-assisted cyclometallation of meta-substituted N-phenyl, N'-methyl, and N-benzyl, N'-methyl imidazolium salts produced mixtures of ortho and para substituted cyclometallated complexes. The study discussed the impact of substituents on isomer ratios, with steric effects playing a more significant role in the 6-membered rings from N-benzyl imidazolium salts compared to the 5-membered rings derived from N-phenyl salts. Comparison was made to steric effects with other common directing groups.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Tulay A. Atesin, William D. Jones, Abdurrahman C. Atesin
Summary: This study investigates the effect of CF3 and CH3 groups on the oxidative addition of benzonitriles' C-CN bond. The results show that the CF3 group stabilizes the oxidative addition products, while the CH3 group destabilizes them. Additionally, there is a slightly larger ortho effect with CF3 compared to F.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Vidmantas Bieliunas, Sigitas Stoncius
Summary: The design and synthesis of second generation C-2-symmetric ligands with additional substituents was reported. These substituents provide a further element for fine-tuning the ligand structure by enforcing conformational rigidity. The tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were successfully employed in the rhodium-catalyzed arylation reaction with good to excellent yields and enantioselectivities up to 99% ee.
Article
Chemistry, Multidisciplinary
E. N. Chulakov, M. A. Korolyova, L. Sh Sadretdinova, A. A. Tumashov, M. Kodess, G. L. Levit, V. P. Krasnov
Summary: The study compared the kinetic resolution of racemic 6-substituted 2-methyl-1,2,3,4-tetrahydroquinolines with acyl chlorides of (S)-naproxen, N-phthaloyl-(S)-leucine, and (R)-O-phenyllactic acid. It was found that the selectivity factors were higher with (S)-naproxen and (R)-O-phenyllactic acid acyl chlorides compared to N-phthaloyl-(S)-leucyl chloride. The stereodifferentiation in the reaction was explained using the DFT method, with aromatic pi-pi interactions playing a key role.
RUSSIAN CHEMICAL BULLETIN
(2021)
Article
Chemistry, Multidisciplinary
Kei Kitamura, Naoyuki Shimada, Craig Stewart, Abdurrahman C. Atesin, Tuelay A. Atesin, Marcus A. Tius
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Inorganic & Nuclear
Tuelay A. Atesin, Abdurrahman C. Atesin, Karlyn Skugrud, William D. Jones
INORGANIC CHEMISTRY
(2008)
Article
Chemistry, Inorganic & Nuclear
Lisa M. Manus, Robert J. Holbrook, Tulay A. Atesin, Marie C. Heffern, Allison S. Harney, Amanda L. Eckermann, Thomas J. Meade
INORGANIC CHEMISTRY
(2013)
Article
Chemistry, Inorganic & Nuclear
Andrew W. Myers, Lingzhen Dong, Tuelay A. Atesin, Roger Skugrud, Christine Flaschenriem, William D. Jones
INORGANICA CHIMICA ACTA
(2008)
Article
Chemistry, Inorganic & Nuclear
Brett D. Swartz, Tuelay A. Atesin, Matthew R. Grochowski, Stephen S. Oster, William W. Brennessel, William D. Jones
INORGANICA CHIMICA ACTA
(2010)
Article
Chemistry, Multidisciplinary
Wei He, Ildiko R. Herrick, Tulay A. Atesin, Patrick A. Caruana, Colleen A. Kellenberger, Alison J. Frontier
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2008)
Article
Chemistry, Inorganic & Nuclear
Tuelay A. Atesin, William D. Jones
Article
Chemistry, Inorganic & Nuclear
Tuelay A. Atesin, Ting Li, Sebastien Lachaize, Juventino J. Garcia, William D. Jones
Article
Chemistry, Inorganic & Nuclear
Tuelay A. Atesin, Sabuj Kundu, Karlyn Skugrud, Katherine A. Lai, Brett D. Swartz, Ting Li, William W. Brennessel, William D. Jones
Article
Chemistry, Physical
David E. Stephens, Johant Lakey-Beitia, Abdurrahman C. Atesin, Tuelay A. Atesin, Gabriel Chavez, Hadi D. Arman, Oleg V. Larionov
Article
Chemistry, Organic
Andrew Quillen, Quynh Nguyen, Matthew Neiser, Kara Lindsay, Alexander Rosen, Stephen Ramirez, Stefana Costan, Nathan Johnson, Thuy Donna Do, Oscar Rodriguez, Diego Rivera, Abdurrahman Atesin, Tulay Aygan Atesin, Lili Ma
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Robert J. Wehrle, Alexander Rosen, Thu Vu Nguyen, Kalyn Koons, Eric Jump, Mason Bullard, Natalie Wehrle, Adam Stockfish, Patrick M. Hare, Abdurrahman Atesin, Tulay A. Atesin, Lili Ma
Summary: A methodology for the synthesis of unsymmetrical heteroaryl 1,2-diketones using enones, a palladium catalyst, and an oxidant is reported. The lowest energy conformations of the synthesized compounds were analyzed using density functional theory.
Article
Chemistry, Inorganic & Nuclear
Sebastien Lachaize, Dominique C. Gallegos, Juliana J. Antonio, Abdurrahman C. Atesin, Tulay A. Atesin, William D. Jones
Summary: The effect of fluoro substitution on the C-C bond activation of aromatic nitriles was investigated using density functional theory calculations and experimental measurements. The results revealed that the stability of the C-C bond activation products is significantly influenced by ortho-F substituents, with a decrease of 6.6 kcal/mol per ortho-F substituent, while the influence of meta-F substituents is relatively small, with a decrease of 1.8 kcal/mol per meta-F substituent.
Article
Chemistry, Multidisciplinary
Tulay A. Atesin, Ting Li, Sebastien Lachaize, William W. Brennessel, Juventino J. Garcia, William D. Jones
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2007)