Article
Chemistry, Inorganic & Nuclear
Philipp C. Stegner, Jonathan Eyselein, Gerd M. Ballmann, Jens Langer, Jochen Schmidt, Sjoerd Harder
Summary: The chiral building block (R)-(+)-2,2 '-diamino-1,1 '-binaphthyl, (R)-BINAM, was converted to N-substituted proligands and alkaline earth metal catalysts. Quadrant models analysis showed that ligands with specific substituents provided the best steric discrimination in enantioselective intramolecular alkene hydroamination reactions.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Young Ho Kim, Dong Bin Kim, Su San Jang, So Won Youn
Summary: A Pd-catalyzed intramolecular allylic C-H amination method has been developed, allowing for the synthesis of diverse 1,3-X,N-heterocycles through selective allylic C-H cleavage and pi-allylpalladium formation. The use of substrates containing a labile allylic moiety and new catalytic systems overcomes significant challenges for achieving highly chemo- and regioselective allylic C-H amination.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Agnieszka J. Nawara-Hultzsch, Anandarup Goswami, Kai C. Hultzsch
Summary: A study on the influence of solvents and additives in enantioselective hydroamination/cyclization reactions showed that weakly coordinating polar solvents can increase reaction rates, while some additives can enhance enantioselectivity in cyclization reactions but decrease selectivity in hydroamination reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Xian Xu, Xizhou Zheng, Xin Xu
Summary: A redox-neutral C-H/N-H annulation of anilines with allenes and dienes was achieved using a scandium catalyst with a simple beta-diketiminato ligand. The reaction selectively produced a family of tetrahydroquinolines in high isolated yields, with both allene and diene coupling partners serving as three-carbon building blocks. Mechanistic investigations suggested a reaction pathway involving N-H allylation, Hofmann-Martius rearrangement, and hydroamination cyclization.
Article
Chemistry, Multidisciplinary
Shengjie Jiang, Yanping Cai, Ambre Carpentier, Iker del Rosal, Laurent Maron, Xin Xu
Summary: This work reports the first catalyzed synthesis of d-block metal-metal bonded complexes. The treatment of terminal zinc hydrides in the presence of 5 mol% Ni(CO)(2)(PPh3)(2) afforded Zn(i)-Zn(i) bonded compounds in high isolated yields with concomitant elimination of dihydrogen. Stoichiometric reactions, kinetic studies and DFT calculations were conducted to elucidate the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Ian A. Tonks
Summary: This study discusses the recent progress in Ti-catalyzed oxidative amination reactions, highlighting the importance of understanding the reactive species and mechanisms involved. The research shows that low-valent Ti intermediates can be stabilized through coordination and that reductive elimination processes occur through pi-type electrocyclic reactions. These findings are crucial for advancing catalytic applications involving titanium.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Jia-Feng Chen, Sajid Ur Rehman, Changkun Li
Summary: A regiodivergent cobalt-catalyzed addition of nucleophiles to allenes has been developed, providing substituted enol esters and branched-allylic products in high yields and with unique selectivities, indicating the distinct reactivity of cobalt compared to rhodium and iridium in allene hydrofunctionalization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ziyi Zhang, Jin Wang, Shenghai Guo, Jing Fan, Xuesen Fan
Summary: We report an efficient strategy for preparing 5H-phthalazino[1,2-b]quinazolin-8(6H)-one derivatives through a t-BuOK-catalyzed intramolecular hydroamination reaction of functionalized quinazolinones. The reaction proceeds under mild conditions and yields the desired products in good to high yields via exclusive 6-exo-dig cyclization. This protocol offers readily available starting materials, broad substrate scope, and high regio- and stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jianbin Li, Amardeep Kumar, Jared C. Lewis
Summary: Despite the unique reactivity of vitamin B(12) and its derivatives, B-12-dependent enzymes remain underutilized in biocatalysis. In this study, the B-12-dependent transcription factor CarH was repurposed to enable non-native radical cyclization reactions. The engineered variant CarH* catalyzes the formation of gamma- and delta-lactams through either redox-neutral or reductive ring closure, showing marked enhancement of reactivity and selectivity compared to the free B-12 cofactor. CarH* also catalyzes an unusual spirocyclization by dearomatization of pendant arenes, producing bicyclic 1,3-diene products instead of the 1,4-dienes provided by existing methods. These results and mechanistic studies highlight the importance of protein scaffolds in controlling B-12 reactivity and expanding the synthetic utility of B-12-dependent enzymes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ming Li, Yuke Li, Wan-Yuan Jia, Guo-Qing Sun, Fan Gao, Guo-Xiao Zhao, Yi-Feng Qiu, Xi-Cun Wang, Yong-Min Liang, Zheng-Jun Quan
Summary: The free radical cyclization reaction is a promising strategy for the formation of ring frameworks. In this study, we report a copper-catalyzed tandem radical cyclization strategy for preparing substituted lactam derivatives. This reaction utilizes a radical coupling approach, allowing a wide range of alkenes and being compatible with primary, secondary, and tertiary radicals. Density functional theory calculations were also performed to gain insights into the reaction mechanism.
Article
Chemistry, Organic
Tingting Cao, Lei Zhu, Jun Huang, Zhen Yang
Summary: This study successfully installed a sterically congested all-carbon quaternary center for the first time via a Pd-catalyzed cascade diarylation, providing a new method for the synthesis of complex organic compounds.
Article
Chemistry, Multidisciplinary
Jacob O. Rothbaum, Alessandro Motta, Yosi Kratish, Tobin J. Marks
Summary: In this study, the mechanism of aldehyde and ketone hydroboration catalyzed by La[N(SiMe3)(2)](3) was investigated, revealing that aldehydes and ketones undergo initial carbonyl oxygen coordination to the acidic La center, followed by ligand-assisted intramolecular hydroboration. The study also identified a bidentate acylamino lanthanide complex associated with the aldehyde hydroboration and an aminomonoboronate-lanthanide complex produced under excess HBpin conditions, providing insights into the ligand-assisted hydroboration pathway and previously unknown catalyst deactivation pathways.
Article
Chemistry, Multidisciplinary
Zhengtian Ding, Yiming Wang, Wenfeng Liu, Yate Chen, Wangqing Kong
Summary: The study presents an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from readily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, demonstrating excellent regio-, enantio-, and diastereoselectivity with a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Jorge Escorihuela, Agusti Lledos, Gregori Ujaque
Summary: Hydroamination, the addition of an N-H bond across a C-C multiple bond, is a reaction with significant synthetic potential. This review focuses on achieving anti-Markovnikov regioselectivity in intermolecular hydroaminations of terminal alkynes and alkenes. The mechanisms and factors that favor anti-Markovnikov regioselectivity are discussed, along with alternative pathways and different catalysts.
Article
Chemistry, Applied
Srinivasarao Yaragorla, Dandugula Sneha Latha, Pallava Rajesh
Summary: The study introduced a simple and efficient One-Pot three-component reaction using tert-propargyl alcohols, primary amines, and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives. A green calcium catalyst was employed to facilitate the formation of β-amino allene intermediate, leading to fully substituted five and six-membered azacyclic compounds through subsequent hydroamination and deacylation reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Xiaoming Zhang, Sven Tobisch, Kai C. Hultzsch
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Multidisciplinary
Alexander L. Reznichenko, Hiep N. Nguyen, Kai C. Hultzsch
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2010)
Article
Chemistry, Multidisciplinary
Xiaoming Zhang, Thomas J. Emge, Kai C. Hultzsch
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2012)
Article
Chemistry, Inorganic & Nuclear
Daniela V. Vitanova, Frank Hampel, Kai C. Hultzsch
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2011)
Article
Chemistry, Multidisciplinary
Alexander L. Reznichenko, Kai C. Hultzsch
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Inorganic & Nuclear
Alexander L. Reznichenko, Thomas J. Emge, Stephan Audoersch, Eric G. Klauber, Kai C. Hultzsch, Bernd Schmidt
Article
Chemistry, Inorganic & Nuclear
Alexander L. Reznichenko, Kai C. Hultzsch
Article
Chemistry, Inorganic & Nuclear
Hiep N. Nguyen, Hyeunjoo Lee, Stephan Audoersch, Alexander L. Reznichenko, Agnieszka J. Nawara-Hultzsch, Bernd Schmidt, Kai C. Hultzsch
Article
Chemistry, Organic
Hiep N. Nguyen, Kai C. Hultzsch
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Natalie Hofmann, Kai C. Hultzsch
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Leonard Homberg, Alexander Roller, Kai C. Hultzsch
Article
Chemistry, Organic
Natalie Hofmann, Leonard Homberg, Kai C. Hultzsch
Review
Chemistry, Organic
Natalie Hofmann, Kai C. Hultzsch
Summary: ADC and HT are powerful tools in the multicomponent formation of N-heterocycles, starting from simple and commercially available reagents. Base metal-catalyzed strategies, using manganese, iron, cobalt, nickel, and copper catalysts, have become increasingly important in recent years. These strategies are highly atom-efficient and environmentally friendly, with no need for further reducing or oxidizing agents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Agnieszka J. Nawara-Hultzsch, Anandarup Goswami, Kai C. Hultzsch
Summary: A study on the influence of solvents and additives in enantioselective hydroamination/cyclization reactions showed that weakly coordinating polar solvents can increase reaction rates, while some additives can enhance enantioselectivity in cyclization reactions but decrease selectivity in hydroamination reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Lara H. Polak, John B. Soltys, Kai C. Hultzsch
Summary: The intermolecular anti-Markovnikov hydroamination of vinylsilanes was successfully achieved using five silyl-substituted ortho-terphenoxide yttrium complexes, resulting in excellent activity and complete anti-Markonikov selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)