Copper-Catalyzed Diboron-Mediated cis-Semi-Hydrogenation of Alkynes under Facile Conditions
Abstract
:1. Introduction
2. Results and Discussions
3. Mechanistic Study
4. Materials and Methods
Experimental Procedures and Characterization of Products
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Entry | Catalyst | Ligand | [B] | Base | Solvent | Yield (%) (Z/E) b |
---|---|---|---|---|---|---|
1 | CuBr | nBu3P | B2pin2 | NaOH | DMF | >98 (91 c, >99:1) |
2 | CuI | nBu3P | B2pin2 | NaOH | DMF | 59 (6:1) |
3 | CuCl | nBu3P | B2pin2 | NaOH | DMF | 40 (2.4:1) |
4 | CuBr2 | nBu3P | B2pin2 | NaOH | DMF | 61 (7.6:1) |
5 | CuBr | Ph3P | B2pin2 | NaOH | DMF | 33 (>99:1) |
6 | CuBr | DPPB | B2pin2 | NaOH | DMF | 49 (>99:1) |
7 | CuBr | Cy3P | B2pin2 | NaOH | DMF | 85 (>99:1) |
8 | CuBr | - | B2pin2 | NaOH | DMF | 79 (4.2:1) |
9 | CuBr | nBu3P | B2(OH)4 | NaOH | DMF | 17 (>99:1) |
10 | CuBr | nBu3P | B2pin2 | LiOtBu | DMF | 92 (19:1) |
11 | CuBr | nBu3P | B2pin2 | Na2CO3 | DMF | 56 (12:1) |
12 | CuBr | nBu3P | B2pin2 | DBU | DMF | 75 (>99:1) |
13 | CuBr | nBu3P | B2pin2 | NaOH | DMSO | 91 (>99:1) |
14 | CuBr | nBu3P | B2pin2 | NaOH | THF | 72 (15:1) |
15 | CuBr | nBu3P | B2pin2 | NaOH | MeCN | 77 (>99:1) |
16 | CuBr | nBu3P | B2pin2 | NaOH | dioxane | 91 (9.5:1) |
17 | CuBr | nBu3P | B2pin2 | NaOH | DME | 80 (10:1) |
18 d | CuBr | nBu3P | B2pin2 | NaOH | DMF | 20 (7.3:1) |
19 e | CuBr | nBu3P | B2pin2 | NaOH | DMF | 64 (21:1) |
20 | - | nBu3P | B2pin2 | NaOH | DMF | 0 |
21 | CuBr | nBu3P | - | NaOH | DMF | 0 |
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Zeng, Y.; Zhang, H.; Ma, D.; Wang, G. Copper-Catalyzed Diboron-Mediated cis-Semi-Hydrogenation of Alkynes under Facile Conditions. Molecules 2022, 27, 7213. https://doi.org/10.3390/molecules27217213
Zeng Y, Zhang H, Ma D, Wang G. Copper-Catalyzed Diboron-Mediated cis-Semi-Hydrogenation of Alkynes under Facile Conditions. Molecules. 2022; 27(21):7213. https://doi.org/10.3390/molecules27217213
Chicago/Turabian StyleZeng, Yuxi, Honggang Zhang, Daofan Ma, and Guangwei Wang. 2022. "Copper-Catalyzed Diboron-Mediated cis-Semi-Hydrogenation of Alkynes under Facile Conditions" Molecules 27, no. 21: 7213. https://doi.org/10.3390/molecules27217213