Efficient Aerobic Oxidative Coupling of Methyl Heteroarenes with Indoles
Direct oxidative coupling of inert C(sp3)−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol feat...
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| Published in | Chemistry : a European journal Vol. 29; no. 5; pp. e202202240 - n/a |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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Wiley
24.01.2023
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| Abstract | Direct oxidative coupling of inert C(sp3)−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry.
A sustainable and environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles was first reported. A series of di‐heteroaryl ketones (26 examples) were obtained in moderate yields (up to 72 % yield), providing a highly atom‐economic approach for synthesizing complex pharmaceutical intermediates from small molecules. A plausible mechanism about cyclic catalysis was proposed and confirmed. |
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| AbstractList | Direct oxidative coupling of inert C(sp3)−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry.
A sustainable and environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles was first reported. A series of di‐heteroaryl ketones (26 examples) were obtained in moderate yields (up to 72 % yield), providing a highly atom‐economic approach for synthesizing complex pharmaceutical intermediates from small molecules. A plausible mechanism about cyclic catalysis was proposed and confirmed. Direct oxidative coupling of inert C(sp 3 )−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α ‐methyl substituted N ‐heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry. Direct oxidative coupling of inert C(sp(3))-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of alpha-methyl substituted N-heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry. Direct oxidative coupling of inert C(sp )-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α-methyl substituted N-heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry. Direct oxidative coupling of inert C(sp3)−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α‐methyl substituted N‐heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry. Direct oxidative coupling of inert C(sp3 )-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α-methyl substituted N-heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry.Direct oxidative coupling of inert C(sp3 )-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α-methyl substituted N-heteroarenes with indoles is reported. A variety of diheteroaryl ketones were prepared in good yields (up to 72 %). This protocol features simple operation and broad substrates scope (26 examples). Significantly, a plausible mechanism about catalytic cycle was proposed, and two key intermediates were confirmed by high resolution mass spectrometry. |
| Author | Wang, Nai‐Xing Zhang, Lei‐Yang Gao, Xue‐Wang Lucan, Dumitra Yan, Zhan Feng, Ke Wu, Yue‐Hua Xing, Yalan |
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| Keywords | FUNCTIONALIZATION indoles oxidative coupling reactions C-H BOND VINYLARENES aerobic coupling reactions C(sp)-H heteroarylacylation C(sp3)−H |
| Language | English |
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| Snippet | Direct oxidative coupling of inert C(sp3)−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α‐methyl... Direct oxidative coupling of inert C(sp(3))-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of alpha-methyl... Direct oxidative coupling of inert C(sp 3 )−H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α ‐methyl... Direct oxidative coupling of inert C(sp )-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α-methyl... Direct oxidative coupling of inert C(sp3 )-H bond has been a great challenge. Herein, an environmentally friendly aerobic oxidative coupling of α-methyl... |
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| SubjectTerms | aerobic coupling reactions C(sp3)−H Catalysis Chemistry Chemistry, Multidisciplinary Coupling heteroarylacylation Hydrogen bonds Indoles Indoles - chemistry Intermediates Ketones Mass spectrometry Mass spectroscopy Oxidative Coupling oxidative coupling reactions Physical Sciences Science & Technology Substrates |
| Title | Efficient Aerobic Oxidative Coupling of Methyl Heteroarenes with Indoles |
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