Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst
Here, we report a highly efficient catalytic species generated from Ph3C+[B(C6F5)4]− by the water mediated Friedel-Crafts type reaction of indoles with carbonyl compounds to afford 3,3′-bisindolylmethanes (BIMs). This scalable method is applicable to a wide variety of carbonyl compounds, including u...
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sg-ntu-dr.10356-1714952023-11-06T15:35:04Z Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst Zhang, Zhenguo Ji, Liang Liu, Xiaoxiao Li, Zhihong Lv, Yongheng Jia, Zhenhua Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Catalytic Species Friedel-Crafts Here, we report a highly efficient catalytic species generated from Ph3C+[B(C6F5)4]− by the water mediated Friedel-Crafts type reaction of indoles with carbonyl compounds to afford 3,3′-bisindolylmethanes (BIMs). This scalable method is applicable to a wide variety of carbonyl compounds, including unprotected sugar molecules and carbonyl compounds derived from drugs and natural products. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University Submitted/Accepted version We thank the financial support from the Start-up Grant of Nanjing Tech University (No. 38274017103 and 38037037). T. P. Loh is thankful for the financial support from the Distinguished University Professor grant (Nanyang Technological University), AcRF Tier 1 grants from the Ministry of Education of Singapore (RG107/19, RG11/20 and RT14/20), and the Agency for Science, Technology and Research (A*STAR) under its MTC Individual Research Grants (IRG). The Donors of the Science and Technology Innovation Research Fellowship in Nanjing is also acknowledged for partial support of this research (No. 51237024) and the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYCX20_1031 and KYCX21_1081). 2023-11-03T00:25:15Z 2023-11-03T00:25:15Z 2022 Journal Article Zhang, Z., Ji, L., Liu, X., Li, Z., Lv, Y., Jia, Z. & Loh, T. (2022). Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst. Organic Chemistry Frontiers, 9(19), 5154-5159. https://dx.doi.org/10.1039/d2qo01081j 2052-4129 https://hdl.handle.net/10356/171495 10.1039/d2qo01081j 2-s2.0-85136490414 19 9 5154 5159 en RG107/19 RG11/20 RT14/20 MTC-IRG Organic Chemistry Frontiers © 2022 The Partner Organisations. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1039/D2QO01081J. application/pdf |
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Science::Chemistry Catalytic Species Friedel-Crafts Zhang, Zhenguo Ji, Liang Liu, Xiaoxiao Li, Zhihong Lv, Yongheng Jia, Zhenhua Loh, Teck-Peng Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| description |
Here, we report a highly efficient catalytic species generated from Ph3C+[B(C6F5)4]− by the water mediated Friedel-Crafts type reaction of indoles with carbonyl compounds to afford 3,3′-bisindolylmethanes (BIMs). This scalable method is applicable to a wide variety of carbonyl compounds, including unprotected sugar molecules and carbonyl compounds derived from drugs and natural products. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Zhang, Zhenguo Ji, Liang Liu, Xiaoxiao Li, Zhihong Lv, Yongheng Jia, Zhenhua Loh, Teck-Peng |
| format |
Article |
| author |
Zhang, Zhenguo Ji, Liang Liu, Xiaoxiao Li, Zhihong Lv, Yongheng Jia, Zhenhua Loh, Teck-Peng |
| author_sort |
Zhang, Zhenguo |
| title |
Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| title_short |
Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| title_full |
Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| title_fullStr |
Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| title_full_unstemmed |
Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph₃C⁺[B(C₆F₅)₄]⁻as the pre-catalyst |
| title_sort |
metal-free synthesis of 3,3′-bisindolylmethanes in water using ph₃c⁺[b(c₆f₅)₄]⁻as the pre-catalyst |
| publishDate |
2023 |
| url |
https://hdl.handle.net/10356/171495 |
| _version_ |
1783955532109840384 |