Article
Chemistry, Organic
Yi-Ming Wei, Xiao-Di Ma, Meng-Fei Wang, Xin-Fang Duan
Summary: Fe-catalyzed difunctionalization of aryl titanates through double C-H activation has been developed. Aryl titanates are arylated via ortho C-H activation, followed by ipso electrophilic trapping of the C-Ti bond. The ortho C-H arylation is promoted by a 1,2-Fe/Ti heterobimetallic arylene intermediate and involves another ortho C-H activation directed by benzamides, esters, and nitriles.
Article
Chemistry, Physical
Sankaran Radhika, Mary Baby Aleena, Gopinathan Anilkumar
Summary: An efficient methodology for the synthesis of 2-aminobenzothiazole derivatives in water catalyzed by Fe(III) has been established. This strategy is mild, base-free, and one-pot, allowing the reaction of various substrates with 2-bromophenyl isothiocyanate under air, resulting in moderate to excellent yields under green conditions. The catalyst can be successfully recovered and recycled several times with minimal loss in efficiency.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Meixia Liu, Huimin Hu, Runbo Sun, Haoyuan Li, Anjun Ding, Xiaoyong Liu, Zhengjiang Fu, Shengmei Guo, Hu Cai
Summary: We present a nickel-catalyzed reductive cross-coupling method to synthesize phosphinic amides from readily available nitroarenes and phosphine oxides. The reaction employs NiCl2/Xantphos as catalyst, zinc as reductant, and TMSCl as additive, delivering various phosphinic amides in moderate to good yields. Notably, a gram-scale synthesis was successfully achieved, making this method practical for the synthesis of phosphinic amides. Mechanistic insights were also obtained from control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Jianyu Dong, Xiuling Chen, Fangyan Ji, Lixin Liu, Lebin Su, Min Mo, Jian-Sheng Tang, Yongbo Zhou
Summary: In the presence of copper salt and molecular oxygen, a simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved, resulting in a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, facilitating the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the need for any additional acids, bases, ligands, etc. This reaction provides a simple, direct, and efficient method for synthesizing functionalized esters, especially aryl benzoates, from readily available starting materials.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ming Li, Cui-Tian Wang, Qiao-Fei Bao, Yi-Feng Qiu, Wan-Xu Wei, Xue-Song Li, Yu-Zhao Wang, Zhe Zhang, Jin-Lin Wang, Yong-Min Liang
Summary: The copper-catalyzed radical cross-coupling of oxime esters and activated alkenes successfully produced cyanoalkylsulfonylated oxindoles and cyanoalkyl amides through an aryl migration strategy, with unique desulfonylation and sulfone addition processes involved. The transformation demonstrates good functional group applicability, enabling the regioselective control of two different quaternary stereocenters by the substituent group of the nitrogen atom.
Article
Chemistry, Applied
Nithin Pootheri, Sunwoo Lee
Summary: A method for preparing 18O-labeled esters through a Ni-catalyzed three-component reaction has been developed. This method exhibits excellent selectivity and compatibility with various amides and alkyl halides, enabling the synthesis of diverse isotopically labeled esters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jiabin Ni, Xiaowen Xia, Wei-Feng Zheng, Zhaobin Wang
Summary: Cyclopropanols and cyclopropylamines are important structural motifs in medicinal chemistry and exhibit diverse reactivities in organic synthesis. However, the development of a general protocol for obtaining these cyclopropyl derivatives from stable and readily available starting materials remains a challenging task due to the high ring strain energy. In this study, a Ti-based catalyst was found to effectively promote the diastereoselective syntheses of cyclopropanols and cyclopropylamines from widely accessible carboxylic derivatives and terminal olefins. This method represents the first example of directly converting alkyl carboxylic acids into cyclopropanols and offers broad substrate scope and good functional group compatibility.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Yujing Li, Huihui Luo, Shuo Wang, Lei Li, Guosong Li, Wen Dai
Summary: An efficient protocol for the oxidative cleavage of C-C bonds in alkynes using heterogeneous cobalt nanoparticles as catalyst with molecular oxygen as the oxidant has been developed. A diverse set of mono- and multisubstituted aromatic and aliphatic alkynes can be effectively cleaved and converted into esters. The high surface area and pore volume, as well as the nanostructured nitrogen-doped graphene-layer coated cobalt nanoparticles, are possibly responsible for excellent catalytic activity.
Article
Chemistry, Multidisciplinary
Tingting Li, Gerald B. Hammond, Bo Xu
Summary: A widely applicable approach to synthesize ketones, esters, and amides via the oxidative C-C bond cleavage of readily available alkyl aldehydes has been developed using green and abundant molecular oxygen as the oxidant, and base metals (cobalt and copper) as catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and alpha-ketoamides from aldehydes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xiao-Qin Shen, Sui-Qian Wang, Dongfeng Fan, Xing-Guo Zhang, Hai-Yong Tu
Summary: A practical and efficient method for synthesizing alpha-fluorothioacrylamide was developed through selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions show excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yasuaki Iyori, Rina Ueno, Aoi Morishige, Naoto Chatani
Summary: The Ni-catalyzed reaction involves annulation of ortho-phenoxy-substituted aromatic amides with alkynes to form 1(2H)-isoquinolinones in the presence of (LiOBu)-Bu-t as a base. The reaction proceeds even without a ligand under mild conditions at 40 degrees C. An electron-donating group on the aromatic ring facilitates the reaction, which is also applicable to various leaving groups such as carbamate, methylthio, and cyano.
Article
Chemistry, Applied
Tao Yi, Quan Liu, Yue Zhang, Jinhao Huang, Zhigang Zeng, Yunfeng Chen
Summary: A copper-catalyzed cascade reaction was reported for the selective oxidative cleavage of C-C bonds in β-alkyl nitroolefins, followed by oxidative amidation with amines or amides. The reaction showed high selectivity and yielded α-ketoamides with 66-88% yields. Mechanistic studies revealed that the reaction occurred on more electron-rich allylic nitro tautomers originating from the equilibrium of conjugated nitroalkenes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hao-Cong Li, Guan-Nan Li, Hao-Sen Wang, Yan Tan, Xiao-Lan Chen, Bing Yu
Summary: A visible-light-induced one-pot three-component reaction was developed for the difunctionalization of alkenes. It showed excellent regioselectivity, broad substrate scope, and high synthetic yield, leading to the synthesis of versatile sulfoximido-cyanoalkylative products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Qing-Qing Kang, Zi-Ying Wang, Sen-Jie Hu, Chun-Mei Luo, Xue-Er Cai, Yong-Bin Sun, Ting Li, Wen-Ting Wei
Summary: Copper-catalyzed cyclization of alkynes plays a significant role in catalytic chemistry. However, the uncontrolled reactivity of the vinyl-Cu-II intermediate limits the selective cyclization in this transformation. This study presents a practical strategy to control the cyclization and oxidative cleavage of the vinyl-Cu-II intermediate, enabling the switchable construction of quinolin-2-ones and quinoline-2,4-diones from alkyne-tethered alpha-bromocarbonyls using a commercially available copper catalyst under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ji-Jia Zhou, Ya-Nan Meng, Li-Gao Liu, Yi-Xi Liu, Zhou Xu, Xin Lu, Bo Zhou, Long-Wu Ye
Summary: The functionalization of etheric C-O bonds via C-O bond cleavage is a promising method for the synthesis of C-C and C-X bonds. However, the enantioselective version of these reactions, mainly involving C(sp(3))-O bond cleavage, is highly challenging. Here, we present a copper-catalyzed asymmetric cascade cyclization, which allows for the efficient and enantioselective synthesis of chromeno[3,4-c]pyrroles with a triaryl oxa-quaternary carbon stereocenter. Notably, this protocol represents the first example of [1,2]-Stevens-type rearrangement via C(sp(2))-O bond cleavage and [1,2]-aryl migration reactions via vinyl cations.
Article
Chemistry, Organic
Jingjing Wang, Wei-Guang Kong, Feng Li, Jie Liu, Qin Shen, Lantao Liu, Wen-Xian Zhao
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Organic
Yuanguang Lin, Weiguang Kong, Qiuling Song
Article
Chemistry, Organic
Qingqing Xuan, Weiguang Kong, Quling Song
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Xuezhao Xu, Bingnan Li, Yingwei Zhao, Qiuling Song
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Organic
Weiguang Kong, Changjiang Yu, Hejun An, Qiuling Song
Article
Chemistry, Organic
Bingnan Li, Shaoyu Mai, Qiuling Song
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Organic
Kaixia Jian, Bingnan Li, Shuxian Zhu, Qingqing Xuan, Qiuling Song
Summary: In this study, a catalyst-free and efficient method using H3N•BH3 for the chemoselective reduction of α,β-unsaturated cycloketones and acyclic α,β-unsaturated ketones is described. The method is expedient, green, and applicable.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Weiguang Kong, Hejun An, Qiuling Song
CHEMICAL COMMUNICATIONS
(2017)
