Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes

Fernanda A. Siqueira; Eloisa E. Ishikawa; Andre Fogaca; Andrea T. Faccio; Vania M. T. Carneiro; Rafael R. S. Soares; Aline Utaka; Iris R. M. Tebeka; Marcin Bielawski; Berit Olofsson; Luiz F. Silva Jr.

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Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes

机译：碘（III）介导的1,2-二氢萘的环状收缩无金属合成茚满

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Um protocolo livre de metais foi desenvolvido para sintetizar indanos atraves da contracao de anel de 1,2-di-hidronaftalenos promovida por PhI(OH)OTs (HTIB ou reagente de Koser). Este rearranjo oxidativo pode ser realizado em diversos solventes (MeOH, CH_3CN, 2,2,2-trifuoroetanol (TFE), 1,1,1,3,3,3-hexafuoroisopropanol (HFIP), e uma mistura 1:4 de TFE:CH_2Cl_2) em condicoes brandas. A contracao de anel fornece indanos trans-1,3-dissubstituidos diastereosseletivamente, os quais sao dificeis de obter em quimica organica sintetica.

机译：开发了一种无金属方案以通过PhI（OH）OTs（HTIB或Koser试剂）促进的1,2-二氢萘环的收缩来合成茚满。可以在几种溶剂（MeOH，CH_3CN，2,2,2-三氟乙醇（TFE），1,1,1,3,3,3-六氟异丙醇（HFIP）和1：4的TFE混合物）中进行这种氧化重排：CH_2Cl_2）在温和的条件下。环收缩提供了非对映选择性的反式1,3-二取代的茚满，这在合成有机化学中很难获得。

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《Journal of the Brazilian Chemical Society》 |2011年第9期|共13页
作者
Fernanda A. Siqueira; Eloisa E. Ishikawa; Andre Fogaca; Andrea T. Faccio; Vania M. T. Carneiro; Rafael R. S. Soares; Aline Utaka; Iris R. M. Tebeka; Marcin Bielawski; Berit Olofsson; Luiz F. Silva Jr.;
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正文语种 eng
中图分类化学;
关键词
indanes; hypervalent iodine; ring contraction; 1; 2-dihydronaphthalenes; rearrangements;

机译：茚满;高碘;环收缩;1;2-二氢萘;重排;

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1. Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes [J] . Fernanda A. Siqueira, Eloisa E. Ishikawa, Andre Fogaca, Journal of the Brazilian Chemical Society . 2011,第9期

机译：碘（III）介导的1,2-二氢萘的环状收缩无金属合成茚满
2. Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction [J] . Ahmad Anees, Silva Luiz F. Jr. The Journal of Organic Chemistry . 2016,第5期

机译：通过手性高价碘（III）介导的环收缩合成茚满的无金属不对称
3. Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction [J] . Ahmad Anees, Silva Luiz F. Jr. The Journal of Organic Chemistry . 2016,第5期

机译：通过手性高价碘（III）介导的环收缩合成茚满的无金属不对称
4. SOLUTION-MEDIATED SYNTHESIS OF A NEW THREE-DIMENSIONALZINCOPHOSPHATE IN THE PRESENCE OF RACEMIC 1,2-DIAMINOPROPANE [C] . Y. XING, Y. L. LIU, G. LI, Hydrothermal Reactions and Techniques . 2003

机译：1,2,2-二氨基丙烷存在下新型三维二维锌磷酸盐的溶液介导合成
5. I. Sulfonium-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-hydroxy-beta-glycosides. II. Hypervalent iodine (III)-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-acyloxy-beta-glycosides. III. Efforts toward the synthesis of immunologic adjuvant QS-21A(api). [D] . Kim, Yong-Jae. 2003

机译：I.硫介导的葡萄糖供体的氧化糖基化反应，用于合成C（2）-羟基-β-糖苷。二。高价碘（III）介导的糖供体的氧化糖基化反应，用于合成C（2）-酰氧基-β-糖苷。三，致力于合成免疫佐剂QS-21A（api）。
6. Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine [O] . Siguara Bastos Lemos Silva, Adriana Della Torre, João Ernesto de Carvalho, 2015

机译：高价碘介导的无金属重排的七元环
7. Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes [O] . Siqueira, Fernanda A., Ishikawa, Eloisa E., Fogaça, André, 2011

机译：碘（III）介导的1,2-二氢萘的环状收缩无金属合成茚满

Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes

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