Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Instrumentation
2.2. General Procedure for Preparation of 2
2.3. General Procedure for Preparation of Tropones 1
2.4. Spectroscopic Characterization
3. Results and Discussion
3.1. Preparation and Optimization of Reaction Conditions
3.2. Reaction Scope
3.3. Photo-Physical Property of Tropones 1
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Complex/Ligand | Base (eq.) | Solvent | Temp./Time | Yield 2 |
---|---|---|---|---|---|
1 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | DMF | 140 °C/20 h | 68% |
2 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | 98% |
3 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (3) | DMF | 140 °C/20 h | 95% |
4 | Pd(OAc)2/PCy3·HBF4 | DBU (1.2) | DMSO | 140 °C/20 h | - |
5 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | DMSO | 140 °C/10 h | 58% |
6 | Pd(OAc)2/PPh3 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | 42% |
7 | Pd(OAc)2/P(o-tol)3 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | 21% |
8 | Pd(OAc)2/PCy3 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | 78% |
9 | Pd(OAc)2 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | - |
10 | Pd(PPh3)4 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | 74% |
11 3 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | DMSO | 140 °C/20 h | - |
12 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | DMSO | 120 °C/20 h | - |
13 | Pd(OAc)2/PCy3·HBF4 | Cs2CO3 (1.2) | toluene | 110 °C/20 h | - |
Compd. | λabs (nm) 2 | λmax (nm) | λemi (nm) | Δλstoke 3 |
---|---|---|---|---|
1aa | 273 (20,002), 363 (11,677) | 363 | 462 | 99 |
1ab | 279 (26,170), 360 (17,098) | 360 | 464 | 104 |
1ac | 275 (19,714), 361 (11,859) | 361 | 447 | 86 |
1ad | 275 (29,226), 362 (15,367) | 362 | 448 | 86 |
1ae | 313 (26,321), 361 (14,403) | 361 | 425 | 64 |
1af | 274 (12,257), 371 (9087) | 371 | 477 | 106 |
1da | 278 (23,794), 358 (15,537) | 358 | 439 | 81 |
1ea | 273 (24,253), 374 (16,325) | 374 | 486 | 112 |
1fa | 282 (29,814), 359 (16,748) | 359 | 464 | 105 |
1ga | 282 (21,399), 368 (16,729) | 368 | 473 | 105 |
Solvent | λabs (nm) 2 | λmax (nm) | λemi (nm) | Δλstoke 3 |
---|---|---|---|---|
Toluene | 292 (14,833), 355 (14,988) | 355 | 426 | 71 |
THF | 296 (15,599), 351 (13,012) | 351 | 393 | 42 |
EtOAc | 276 (30,563), 351 (19,608) | 351 | 396 | 45 |
EtOH | 275 (29,226), 362 (15,367) | 362 | 448 | 86 |
CH3CN | 276 (28,451), 353 (17,793) | 353 | 433 | 80 |
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Lin, Y.-W.; Liu, S.-T. Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization. Reactions 2024, 5, 111-119. https://doi.org/10.3390/reactions5010005
Lin Y-W, Liu S-T. Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization. Reactions. 2024; 5(1):111-119. https://doi.org/10.3390/reactions5010005
Chicago/Turabian StyleLin, Yu-Wei, and Shiuh-Tzung Liu. 2024. "Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization" Reactions 5, no. 1: 111-119. https://doi.org/10.3390/reactions5010005