Synthesis of 1,3-Diynes via Cadiot–Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes
- Phil C. KnutsonPhil C. KnutsonDepartment of Chemistry, University of Georgia, Athens, Georgia 30602, United StatesMore by Phil C. Knutson
- ,
- Haleigh E. FredericksHaleigh E. FredericksDepartment of Chemistry, University of Georgia, Athens, Georgia 30602, United StatesMore by Haleigh E. Fredericks
- , and
- Eric M. Ferreira*Eric M. Ferreira*E-mail: [email protected]Department of Chemistry, University of Georgia, Athens, Georgia 30602, United StatesMore by Eric M. Ferreira
Abstract
A convenient Cadiot–Chodkiewicz protocol that facilitates the use of low molecular weight alkyne coupling partners is described. The method entails an in situ elimination from a dibromoolefin precursor and immediate subjection to copper-catalyzed conditions, circumventing the hazards of volatile brominated alkynes. The scope of this method is described, and the internal 1,3-diyne products are preliminarily evaluated in ruthenium-catalyzed azide-alkyne cycloadditions.
Cited By
This article is cited by 12 publications.
- Yi-An Liao, Wen-Sheng Peng, Ling-Jun Liu, Ting-You Ye, Jun-Hao Fu, Yi-Tsu Chan, Fu-Yu Tsai. Iron-Catalyzed Cadiot–Chodkiewicz Coupling with High Selectivity in Water under Air. The Journal of Organic Chemistry 2022, 87 (21) , 13698-13707. https://doi.org/10.1021/acs.joc.2c01354
- Amol D. Sonawane, Yasuhiro Kubota, Mamoru Koketsu. Iron-Promoted Intramolecular Cascade Cyclization for the Synthesis of Selenophene-Fused, Quinoline-Based Heteroacenes. The Journal of Organic Chemistry 2019, 84 (13) , 8602-8614. https://doi.org/10.1021/acs.joc.9b01061
- Yi-Lin Zhao, Yong Yao, Wan-Ting Li, Jing-Hao Qin, Qing Sun, Jin-Heng Li, Xuan-Hui Ouyang. Copper-catalyzed functionalization/transformation of styrenes with polyhaloalkanes and arenes enables the synthesis of heteroarene-containing gem -dihaloalkenes. Organic Chemistry Frontiers 2023, 10 (19) , 4809-4815. https://doi.org/10.1039/D3QO01040F
- Jie Liu, Yao Zhu, Jun Luo, Ziyi Zhu, Lin Zhao, Xiaoyan Zeng, Dongdong Li, Jun Chen, Xiaobing Lan. A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction. Molecules 2023, 28 (13) , 5083. https://doi.org/10.3390/molecules28135083
- Subhankar Ghosh, Shital Kumar Chattopadhyay. Transition-Metal-Free Synthesis of Symmetrical 1,4-Diarylsubstituted 1,3-Diynes by Iodine-Mediated Decarboxylative Homocoupling of Arylpropiolic Acids. Tetrahedron Letters 2022, 102 , 153908. https://doi.org/10.1016/j.tetlet.2022.153908
- Jun Tang, Bowen Jiao, Wei Chen, Fei Ruan, Fengfeng Li, Peixin Cui, Chao Wan, Minh Ngoc Ha, Van Noi Nguyen, Qingping Ke. Revealing efficient catalytic performance of N-CuOx for aerobic oxidative coupling of aliphatic alkynes: A Langmuir—Hinshelwood reaction mechanism. Nano Research 2022, 15 (7) , 6076-6083. https://doi.org/10.1007/s12274-022-4323-5
- Fall Lamine, C. M. A. Afsina, Rajan Archana, Gopinathan Anilkumar. Recent Advances in Palladium-catalyzed Borylation. Current Catalysis 2022, 11 (1) , 16-40. https://doi.org/10.2174/2211544711666220629110020
- Shaheera Tabassum, Ameer Fawad Zahoor, Sajjad Ahmad, Razia Noreen, Samreen Gul Khan, Hamad Ahmad. Cross-coupling reactions towards the synthesis of natural products. Molecular Diversity 2022, 26 (1) , 647-689. https://doi.org/10.1007/s11030-021-10195-6
- Xuelun Duan, Nan Zheng, Ming Li, Xinhao Sun, Zhuye Lin, Pan Qiu, Wangze Song. Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes. Chinese Chemical Letters 2021, 32 (12) , 4019-4023. https://doi.org/10.1016/j.cclet.2021.05.037
- Sayan Sarkar, Piyali Sarkar, Sandip Munshi, Pradyut Ghosh. One‐Pot Dual C−C Coupling Reaction via Site Selective Cascade Formation by Pd II ‐Cryptate of an Amino‐Ether Heteroditopic Macrobicycle. Chemistry – A European Journal 2021, 27 (25) , 7307-7314. https://doi.org/10.1002/chem.202005397
- Eric M. Ferreira, Eric T. Newcomb, Phil C. Knutson. Cycloisomerizations across three states: the total synthesis of gelsenicine. 2021, 177-209. https://doi.org/10.1016/B978-0-12-822212-6.00005-9
- Sankaran Radhika, Nissy Ann Harry, Mohan Neetha, Gopinathan Anilkumar. Recent trends and applications of the Cadiot–Chodkiewicz reaction. Organic & Biomolecular Chemistry 2019, 17 (41) , 9081-9094. https://doi.org/10.1039/C9OB01757G