Article
Chemistry, Multidisciplinary
Tingrui Li, Yilitabaier Julaiti, Xiaopeng Wu, Jie Han, Jin Xie
Summary: The gold-catalyzed ring-opening rearrangement of cyclopropenes provides an efficient method for synthesizing polysubstituted naphthols or aryl-substituted furans. The reaction selectivity between naphthols and furans can be switched by using different gold-carbenes or gold-carbocations as catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Bin Shi, Jia-Bin Liu, Ze-Tian Wang, Liang Wang, Yu Lan, Liang-Qiu Lu, Wen-Jing Xiao
Summary: This study presents a new method for the synthesis of chiral endocyclic allenes with high efficiency and enantioselectivity, using a relay strategy that combines Pd-catalyzed [3+2] annulation and enyne-Cope rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Camille Van Wesemael, Nicolas Brach, Mihaela Gulea, Gaelle Blond
Summary: A series of 3-allenyl benzo[b]thiophenes were synthesized through a gold(I)-catalyzed domino reaction. The process involves a 5-endo-dig cyclization with C S bond formation and consecutive S-to-C propargyl migration via [3,3]-sigmatropic Claisen rearrangement. Various fused O-heterocycles can be obtained from a substrate bearing a 3-butynol moiety via intramolecular hydroalkoxylation. The gold-mediated 1,3-migration involving allenyl to propargyl rearrangement is also described.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Minghao Wang, Julie C. Simon, Mengfei Xu, Stephanie A. Corio, Jennifer S. Hirschi, Vy M. Dong
Summary: Chiral N-cyclopropyl pyrazoles and related heterocycles were synthesized using a copper catalyst under mild conditions, showing high control over regio-, diastereo-, and enantioselectivity. The preference for N-2 over N-1 regioselectivity in the pyrazole was observed. Experimental and DFT studies suggest a unique mechanism involving a five-centered aminocupration.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Song-Zhou Cai, Rongrong Yu, Can Li, Hongyu Zhong, Xichang Dong, Bill Morandi, Juntao Ye, Xianjie Fang
Summary: Hydrothiocarbonylation of olefins using carbon monoxide and thiols is a powerful method to synthesize thioesters. However, transition-metal-catalyzed asymmetric thiocarbonylation, particularly with earth abundant metals, is rarely reported. In this study, a nickel-catalyzed enantioselective hydrothiocarbonylation of cyclopropenes was developed for the synthesis of functionalized thioesters with high stereoselectivity.
Article
Chemistry, Multidisciplinary
Zhi-Lin Zhang, Zhen Li, Yuan-Tai Xu, Lu Yu, Jian Kuang, Yan Li, Jia-Wang Wang, Changlin Tian, Xi Lu, Yao Fu
Summary: In this study, a low-valent CoH-catalyzed facial-selective cyclopropene hydroalkylation was developed, providing a promising approach for accessing multi-substituted cyclopropanes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Zepeng Zhang, Yunpeng Gao, Shufeng Chen, Jianbo Wang
Summary: Cyclopropenes, as the smallest unsaturated cyclic compounds in nature, are important synthetic intermediates in organic chemistry and unique monomers in polymerization. Recent research has focused on the polymerization reactions of cyclopropenes, including addition polymerization and ring-opening metathesis polymerization (ROMP), with promising prospects for future development in polymer synthesis methodology.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Guanghui Wang, Ximei Zhao, Jian Jia, Zengzeng Li, Haotian Li, Yongqiang Wang
Summary: This study presents a zinc-catalyzed method for inserting vinyl carbenes generated from cyclopropenes into the B-H bonds of Lewis base-borane adducts, providing a concise and efficient route to allylboranes. The use of inexpensive and low-toxicity ZnCl2 as the catalyst allows for high-yielding allylboranes with excellent E/Z ratios. Moreover, this method offers a broader scope of Lewis base-borane adducts compared to other catalytic methods for metal carbene insertion into B-H bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Palasetty Chandu, Sourabh Biswas, Sumit Garai, Devarajulu Sureshkumar
Summary: In this study, we present an efficient method for the synthesis of poly-substituted sulfonated cyclopropane derivatives using sodium sulfinates. The method shows broad applicability, scalability, and compatibility with late-stage functionalization, with good tolerance towards diverse functional groups.
Article
Chemistry, Organic
Satoshi Kishida, Misaki Takano, Takuya Sekiya, Yutaka Ukaji, Kohei Endo
Summary: This paper presents a synthetic method for the synthesis of 1,2,4,5-tetraarylbenzene derivatives using cyclopropenes as starting materials. Through Lewis acid-mediated dimerization, cyclopropenes are transformed into tricyclo[3.1.0.02,4]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions yields 1,4-cyclohexadienes bearing quaternary carbons. The novel Br2-mediated oxidative rearrangement of 1,4-cyclohexadienes results in the formation of 1,2,4,5-tetraarylbenzene derivatives with high to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wo Nie, Shichao Shen, Cheng Ma
Summary: A rhodium-catalyzed dehydrogenative cycloisomerization of dienylcyclopropane compounds is reported, providing a straightforward approach to highly substituted toluene derivatives in yields of 67-85%. The dienylcyclopropaneimides are produced through a single-step olefination procedure. Preliminary mechanistic studies suggest that an electron-withdrawing group as R is crucial for completing this transformation.
Article
Chemistry, Organic
Ming Huang, Changsheng Zhou, Ke-Fang Yang, Ze Li, Guo-Qiao Lai, Pinglu Zhang
Summary: This study developed an effective catalyst for the hydroborylation of cyclopropenes, resulting in the formation of cyclopylboronates that can be transformed into versatile cyclopropanes. This method works under mild reaction conditions in an open-air atmosphere and can be easily scaled up. Control experiments provide key insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rongrong Yu, Song-Zhou Cai, Can Li, Xianjie Fang
Summary: In this study, a nickel-catalyzed asymmetric carbonylation reaction was reported for the rapid construction of polysubstituted cyclopropanecarboxylic derivatives. The method exhibited high atom economy, good functional group tolerance, and excellent diastereo- and enantioselectivity. The synthetic utility of the method was demonstrated by facile conversion of the chiral products into bioactive molecules such as (-)-Tranylcypromine and (-)-Lemborexant.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ryota Sakamoto, Minami Odagi, Masahiro Yamanaka, Kazuo Nagasawa
Summary: We report a 1,3-boron shift-type reaction occurring at the center (sp) carbon in allenes to generate 2-boryl-1,3-dienes with diverse substituents. Notably, this reaction takes place in situ with allenylboronates in the presence of carbamate and a small excess of sec-BuLi, eliminating the need for isolating the unstable homoallenylboronates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
He Zhang, Linjuan Jiang, Mei Yang, Yuanhong Liu
Summary: A general and practical route for silylation of propargyl carbonates with silylboranes catalyzed by copper has been developed. Various propargyl carbonates with different substitution patterns are compatible with this catalytic system, allowing for the synthesis of diverse silylallenes efficiently and with functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2023)
