Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. General Procedure for the Photoinduced Bisphosphination of Alkynes with Tetraphenyldiphosphine Monosulfide
3.3. Base-Catalyzed Double Bond Isomerization of vic-1,2-Bisphosphinoalkenes 5a
3.4. Base-Catalyzed Double Bond Isomerization of vic-1,2-Bisphosphinoalkenes 5b
3.5. X-ray Diffraction Studies of 6b
3.6. Base-Catalyzed Double Bond Isomerization of vic-1,2-Bisphosphinoalkenes 4f
4. 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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Time (h) | Yield 3a (%) a | E-Selectivity (%) | ||
E | Z | |||
0.5 | 19 | 0.2 | 99 | |
1.0 | 28 | 1 | 97 | |
1.5 | 34 | 1 | 97 | |
2.0 | 39 | 1 | 98 | |
3.5 | 47 | 2 | 96 | |
6.0 | 52 | 3 | 95 | |
9.0 | 55 | 5 | 92 | |
13 | 56 | 7 | 89 |
Time (h) | Yield 3b (%) a | E-Selectivity (%) | ||
E | Z | |||
0.5 | 41 | 2 | 95 | |
1.0 | 51 | 3 | 94 | |
2.0 | 65 | 8 | 89 | |
4.5 | 64 | 14 | 82 | |
6.0 | 61 | 19 | 76 | |
12 | 52 | 32 | 62 |
Entry | Alkyne 2 | 3 | Yield (%) a [E/Z] | Product 4 | Yield (%) b [E/Z] |
1 c | 57 [91/9] | 63 [90/10] | |||
2 d | 67 [90/10] | 62 [90/10] | |||
3 c | 58 [91/9] | 48 [100/0] | |||
4 c | 41 [90/10] | 42 [89/11] | |||
5 c | 50 [90/10] | 57 [90/10] | |||
6 c | 56 [89/11] | 50 [98/2] | |||
7 c | complex mixture | - | - | - | |
8 c | overlapped | 54 [91/9] | |||
9 d | 62 e | 65 [99/1] | |||
10 d | 67 [90/10] | 64 [100/0] |
Entry | Base (mol%) | Solvent | Temp. (°C) | Yield (%) a | |
6a [E/Z] | 6a’ | ||||
1 | nOct–NH2 (100) | CH3CN | 80 | 90 [87/13] | 6 |
2 | nOct–NH2 (20) | Toluene | 110 | 90 [87/13] (42) | 6 |
3 b | nOct–NH2 (5) | Toluene | 110 | 29 [83/17] | N. D. |
4 b | DBU (5) | Toluene | 110 | 59 [88/12] | 39 |
5 | DBU (40) | Toluene | 110 | 15 [93/7] | 83 (56) |
6 | - | Toluene | 110 | N. D. | N. D. |
Entry | Base (mol%) | Solvent | Temp. (°C) | Yield 6b (%) a |
1 | nOct-NH2 (100) | CH3CN | 80 | 74 |
2 | nBu-NH2 (100) | CH3CN | 80 | 62 |
3 | iPr2NH (100) | CH3CN | 80 | 4 |
4 | iPr2NEt (100) | CH3CN | 80 | trace |
5 | Et3N (100) | CH3CN | 80 | 2 |
6 | DBU (100) | CH3CN | 80 | 94 |
7 | DMAP (100) | CH3CN | 80 | 23 |
8 | Cs2CO3 (100) | CH3CN | 80 | trace |
9 | nOct-NH2 (20) | Toluene | 110 | 94 |
10 | DBU (20) | Toluene | 110 | 98 |
11 b | DBU (5) | Toluene | 110 | 99 (95) |
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Yamamoto, Y.; Tanaka, R.; Kodama, S.; Nomoto, A.; Ogawa, A. Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization. Molecules 2022, 27, 1284. https://doi.org/10.3390/molecules27041284
Yamamoto Y, Tanaka R, Kodama S, Nomoto A, Ogawa A. Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization. Molecules. 2022; 27(4):1284. https://doi.org/10.3390/molecules27041284
Chicago/Turabian StyleYamamoto, Yuki, Ryo Tanaka, Shintaro Kodama, Akihiro Nomoto, and Akiya Ogawa. 2022. "Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization" Molecules 27, no. 4: 1284. https://doi.org/10.3390/molecules27041284