Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions
An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good...
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2021
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/147493 |
| _version_ | 1826118010248626176 |
|---|---|
| author | Zhi, Man-Ling Chen, Bing-Zhi Deng, Wei Chu, Xue-Qiang Loh, Teck-Peng Shen, Zhi-Liang |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhi, Man-Ling Chen, Bing-Zhi Deng, Wei Chu, Xue-Qiang Loh, Teck-Peng Shen, Zhi-Liang |
| author_sort | Zhi, Man-Ling |
| collection | NTU |
| description | An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease. |
| first_indexed | 2024-10-01T04:36:45Z |
| format | Journal Article |
| id | ntu-10356/147493 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:36:45Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1474932021-04-05T01:56:22Z Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions Zhi, Man-Ling Chen, Bing-Zhi Deng, Wei Chu, Xue-Qiang Loh, Teck-Peng Shen, Zhi-Liang School of Physical and Mathematical Sciences Science::Chemistry In-situ Generation Aryl Halides An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease. Nanyang Technological University We gratefully acknowledge the financial support from Nanjing Tech University (Start-up Grant No. 39837118, 39837101, and 39837146), the SICAM Fellowship from Jiangsu National Synergetic Innovation Center for Advanced Materials, and Nanyang Technological University. 2021-04-05T01:56:22Z 2021-04-05T01:56:22Z 2019 Journal Article Zhi, M., Chen, B., Deng, W., Chu, X., Loh, T. & Shen, Z. (2019). Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions. The Journal of Organic Chemistry, 84(5), 3017-3023. https://dx.doi.org/10.1021/acs.joc.9b00204 0022-3263 0000-0002-2936-337X https://hdl.handle.net/10356/147493 10.1021/acs.joc.9b00204 30721056 2-s2.0-85061933464 5 84 3017 3023 en The Journal of Organic Chemistry © 2019 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry In-situ Generation Aryl Halides Zhi, Man-Ling Chen, Bing-Zhi Deng, Wei Chu, Xue-Qiang Loh, Teck-Peng Shen, Zhi-Liang Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title | Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title_full | Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title_fullStr | Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title_full_unstemmed | Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title_short | Preparation of alkyl indium reagents by iodine-catalyzed direct indium insertion and their applications in cross-coupling reactions |
| title_sort | preparation of alkyl indium reagents by iodine catalyzed direct indium insertion and their applications in cross coupling reactions |
| topic | Science::Chemistry In-situ Generation Aryl Halides |
| url | https://hdl.handle.net/10356/147493 |
| work_keys_str_mv | AT zhimanling preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions AT chenbingzhi preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions AT dengwei preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions AT chuxueqiang preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions AT lohteckpeng preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions AT shenzhiliang preparationofalkylindiumreagentsbyiodinecatalyzeddirectindiuminsertionandtheirapplicationsincrosscouplingreactions |