| 1. |
- Ahmad, Anees, et al.
(författare)
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Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)
- 2013
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Ingår i: Tetrahedron Letters. - : Elsevier BV. - 0040-4039 .- 1359-8562. ; 54:43, s. 5818-5820
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Tidskriftsartikel (refereegranskat)abstract
- A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser's reagent]. Additionally, an alternative protocol for the synthesis of 1-methyl-2-tetralone through the one-step epoxidation/rearrangement of 4-methyl-1,2-dihydronaphthalene using mCPBA and TsOH was developed.
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| 2. |
- Jalalian, Nazli, et al.
(författare)
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Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts
- 2011
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Ingår i: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011. - : American Chemical Society.
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Konferensbidrag (övrigt vetenskapligt/konstnärligt)abstract
- Diaryl ethers are common structural features in numerous natural products and biol. active compds. Despite more than a century of immense focus on finding efficient synthetic routes to this compd. class, diaryl ethers remain difficult to obtain. Routes that are catalytic in copper have been developed, but high catalyst loadings, excess reagents, elevated temps. and long reaction times are still needed. Pd-catalyzed cross-couplings of phenols and aryl halides at temps. up to 100 °C have recently been reported to give high yields of diaryl ethers. Diaryliodonium salts are non-toxic alternatives to transition metals in the synthesis of diaryl ethers and we have recently developed effective synthetic routes to these salts. Herein we report a fast, high-yielding synthesis of diaryl ethers. The reaction conditions are mild, metal-free, and avoid the use of halogenated solvents, additives, or excess reagents. Precautions to avoid air or moisture are not needed. The scope includes ortho- and halo-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols .
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| 3. |
- Jalalian, Nazli, 1982-, et al.
(författare)
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Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts
- 2011
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Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 13:6, s. 1552-1555
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Tidskriftsartikel (refereegranskat)abstract
- A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky orthosubstituteddiaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, racemization-prone amino acid derivatives,and heteroaromatics are also tolerated. The methodology is expected to be of high utility in the synthesis of complex molecules and in thepharmaceutical industry.
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| 4. |
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| 5. |
- Merritt, Eleanor A., et al.
(författare)
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Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides
- 2010
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 75:21, s. 7416-7419
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Tidskriftsartikel (refereegranskat)abstract
- The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.
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| 6. |
- Silva, Luiz F., Jr., et al.
(författare)
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Hypervalent iodine reagents in the total synthesis of natural products
- 2011
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Ingår i: Natural product reports (Print). - : Royal Society of Chemistry (RSC). - 0265-0568 .- 1460-4752. ; 28:10, s. 1722-1754
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Forskningsöversikt (refereegranskat)abstract
- This report describes the recent applications of hypervalent iodine reagents in the total synthesis of natural products. The large diversity of high-yielding and chemoselective reactions that can be achieved, even for highly functionalized molecules, is summarized, demonstrating that hypervalent iodine reagents have become an essential tool in synthetic organic chemistry.
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| 7. |
- Siqueira, Fernanda A., et al.
(författare)
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Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes
- 2011
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Ingår i: Journal of the Brazilian Chemical Society. - 0103-5053 .- 1678-4790. ; 22:9, s. 1795-1807
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Tidskriftsartikel (refereegranskat)abstract
- A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser’s reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.
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