Article
Chemistry, Organic
Yunxin Sun, Ningning Song, Yanchen Han, Shengtao Ding
Summary: In this study, the regiospecific hydrothiolation of electron-rich thioalkynes with exclusive stereoselectivity was achieved under the facilitation of an organic base. The reaction proceeded rapidly at room temperature and under ambient atmosphere, leading to the formation of beta trans addition products in nearly quantitative yields. The dual nature of the sulfur atom was found to play a crucial role in determining the regio- and stereoselectivity of the reaction. This system demonstrated excellent tolerance towards a wide range of thiols and thioalkynes, highlighting its potential in polymer synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lucas Popek, Jorge Juan Cabrera-Trujillo, Vincent Debrauwer, Nicolas Blanchard, Karinne Miqueu, Vincent Bizet
Summary: This article describes a fully regio- and stereoselective hydroelementation reaction of SF5-alkynes with N, O, and S-nucleophiles, and the further functionalization of the resulting Z-(hetero)vinyl-SF5 intermediates. This reaction provides a suitable platform for accessing alpha-SF5 ketones and esters, as well as beta-SF5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF5- and CF3-alkynes have been conducted to highlight and explain the observed differences in reactivity and selectivity between these two fluorinated motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Wen-Tao Li, Meng-Yang Hu, Jun-Wen Xiong, Xin-Yu Zhang, Shou-Fei Zhu
Summary: This study reports the first iron-catalysed hydroalumination of internal alkynes, highlighting the advantages of this protocol including unusual regioselectivity, broad substrate scope, and good functional group tolerance. The products obtained from this method can be used for the synthesis of bioactive compounds.
Article
Chemistry, Multidisciplinary
Wei-Dong Zhang, Jia-Yu Zou, Qin Zhong, Shi-Sen Li, Jian Zhao
Summary: A simple and cost-effective Pd/Cu-catalyzed borylation of allenylic carbonates with B(2)Pin(2) was developed, providing high yields of 2-boryl 1,3-butadienes under mild conditions. Additionally, the use of different diboron reagents in the reaction was also demonstrated.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xin Huang, Bing-Zhi Chen, Pengbin Li, Ding-Wei Ji, Jinxian Liu, Hao Zheng, Sa-Na Yang, Yan-Cheng Hu, Boshun Wan, Xiang-Ping Hu, Chunling Fu, Yankai Huang, Jian Zheng, Qing-An Chen, Shengming Ma
Summary: This article reports an efficient palladium-catalyzed coupling protocol for the rapid assembly of symmetric butafulvene derivatives. Two complementary mechanisms involving palladium catalysis were confirmed through mechanistic studies, enabling the synthesis of non-symmetric butafulvenes. The advantages of this strategy include mild reaction conditions, simple catalytic systems, and easy scalability. The synthetic potential of the products as platform molecules for cyclobutene derivatives was also demonstrated.
Article
Chemistry, Organic
Rui-Han Niu, Jing Zhang, Ru-Yuan Zhao, Quan-Jian Luo, Jin-Heng Li, Bo Sun
Summary: A cobalt(III)-catalyzed directed C-7 alkynylation of indolines with easily accessible bromoalkynes has been developed, which provides a powerful route for the synthesis of 7-alkynyl-substituted indolines with broad substrate scope and excellent yields. Furthermore, the reaction can also be applied to the coupling of N-aryl 7-azaindoles, demonstrating the synthetic practicability of this strategy.
Article
Chemistry, Physical
Vivek Aryal, Lucas J. Chesley, Doleshwar Niroula, Rishi R. Sapkota, Roshan K. Dhungana, Ramesh Giri
Summary: We have disclosed a novel Ni-catalyzed alkylarylation reaction of electron-deficient alkenes, which allows the construction of two carbon-carbon bonds. The electron-deficient alkenes play a crucial role in stabilizing reaction intermediates and enhancing the catalytic rates. This reaction is also applicable to secondary alkylzinc reagents and internal alkenes, and exhibits excellent regio- and stereocontrol, leading to products with up to three contiguous all-carbon all-cis secondary stereocenters.
Article
Multidisciplinary Sciences
Zi-Lu Wang, Qi Li, Meng-Wei Yang, Zhao-Xin Song, Zhen-Yu Xiao, Wei-Wei Ma, Jin-Bo Zhao, Yun-He Xu
Summary: A copper-catalyzed ligand-controlled selective 1,2- and 1,4-hydrosilylation of 1,3-enynes was reported, which achieved enantiomerically enriched propargyl- and 1,2-allenylsilane products in high yields and excellent enantioselectivities. The reaction showed broad substrate scope and excellent regioselectivities, with mechanistic studies revealing the importance of allenylcopper as the reactive intermediate and the role of ligand in controlling the regioselectivity switch. The high enantiocontrol in the 1,4-hydrosilylation was also explained by DLPNO-CCSD(T) calculations.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jianwen Jin, Andres Felipe Leon Rojas, Yichao Zhao, Sara Helen Kyne, Bo Xia, Bingwei Zhong, Philip Wai Hong Chan
Summary: This study presents a synthetic method for efficiently preparing (E)-3-arylazoindoles, which does not require the exclusion of air or moisture and can be conducted under mild reaction conditions. The suggested mechanistic pathway of the azo coupling reaction reveals the unique electrophilic behavior of α-diazocarbonyl compounds. Experimental studies provide insights into the preferential generation of a (1H-indol-3-yl)gold species and its impact on the regio- and chemoselectivity of the products. The utility of this synthetic method has been demonstrated in the synthesis of specific molecules, molecular switch assembly, and late-stage functionalization of biologically relevant molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Liang Ma, Luyao Kou, Feng Jin, Xionglve Cheng, Suyan Tao, Gangzhong Jiang, Xiaoguang Bao, Xiaobing Wan
Summary: This study reports a novel method for the efficient synthesis of isoxazolines with various functional groups, including the generation of five tricyclic isoxazolines, which has been validated through robust experimental trials. These transformations proceed through the in situ formation of acyclic nitronates, concerted cycloaddition, and group elimination processes to achieve regio- and stereospecificity.
Article
Chemistry, Organic
Tongxu Xiang, Yongze Liu, Qiaoling Xu, Kehan He, Fei Pan
Summary: In this study, we developed a novel synthetic method for regio- and diastereoselective difluoromethylthiolation of acrylamides using palladium catalysis. The reaction exhibited high efficiency and showed good functional group tolerances under mild conditions, allowing access to compounds with SCF2H-containing skeletons. Mechanistic studies and post-functionalization of the product reactions were also conducted to provide insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sudip Shit, Bipin Kumar Behera, Subhamoy Biswas, Anil K. K. Saikia
Summary: A metal-free Lewis acid-initiated protocol has been developed for the synthesis of highly substituted 3-(dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines. The reaction involves the formation of dihydrofuranylidene carbocation followed by intramolecular cyclization, leading to the desired products in moderate to good yields. The methodology can also be extended to the synthesis of 3-(dihydro-2H-pyran-3(4H)-ylidene)-isobenzofuran-1(3H)-imines, and furanylidene isobenzofuranones can be obtained in excellent yields through post synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Manash Protim Gogoi, Rajeshwer Vanjari, B. Prabagar, Shengwen Yang, Shubham Dutta, Rajendra K. Mallick, Vincent Gandon, Akhila K. Sahoo
Summary: A novel synthetic reaction is reported in this study, which introduces a sulfide moiety and an allyl group into ynamides to produce highly substituted thioamino-skipped-dienes with broad substrate scope, while maintaining complete atom economy. The reaction can also be extended to the synthesis of selenoamino dienes, providing insights into the reaction mechanism through DFT studies and control experiments.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Malavath Ratanlal, Jayaram Vankudoth, Gangavaram V. M. Sharma, Maruti A. Mali, Bertrand Carboni, Fabienne Berree, Subhash Ghosh
Summary: An efficient stereo-controlled synthesis method using sequential Suzuki-Miyaura coupling reactions from easily prepared 1-alkene-1,2-diboronic esters and alkynyl bromides to obtain enyne and enediyne derivatives is reported. The resulting enyne boronic esters were further subjected to Borono-Mannich and Suzuki coupling reactions independently to obtain a,ss-unsaturated aminoester and tri-substituted olefin derivatives, respectively. Additionally, divergent syntheses of triazole and cyclopropylboronate derivatives were also presented.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Swetha Jos, Connor Szwetkowski, Carla Slebodnick, Robert Ricker, Ka Lok Chan, Wing Chun Chan, Udo Radius, Zhenyang Lin, Todd B. Marder, Webster L. Santos
Summary: A transition metal-free, regio- and stereo-selective, phosphine-catalyzed method for the synthesis of (E)-1-boryl-1,3-enynes has been reported in this paper. The reaction proceeds with high selectivity for boron addition to the external carbon of the 1,3-diyne framework.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Nimmakuri Rajesh, Dipak Prajapati
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Nimmakuri Rajesh, Dipak Prajapati
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Yuvaraj Dommaraju, Somadrita Borthakur, Nimmakuri Rajesh, Dipak Prajapati
Article
Chemistry, Organic
Nimmakuri Rajesh, Nagaraju Barsu, Basker Sundararaju
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Nimmakuri Rajesh, Basker Sundararaju
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Rupam Sarma, Nimmakuri Rajesh, Dipak Prajapati
CHEMICAL COMMUNICATIONS
(2012)
Article
Chemistry, Organic
Nimmakuri Rajesh, Rupam Sarma, Dipak Prajapati
Article
Chemistry, Multidisciplinary
Nimmakuri Rajesh, Rupam Sarma, Dipak Prajapati
Article
Chemistry, Multidisciplinary
Malay Sen, Nimmakuri Rajesh, Balakumar Emayavaramban, J. Richard Premkumar, Basker Sundararaju
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
