Synthesis and reactivity of alpha-phenylseleno-beta-substituted styrenes. Preparation of (Z)-allyl alcohols, (E)-alpha-phenyl-alpha,beta-unsaturated aldehydes and alpha-aryl acetophenones

Lenardao EJ; Cella R; Jacob RG; da Silva TB; Perin G

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Synthesis and reactivity of alpha-phenylseleno-beta-substituted styrenes. Preparation of (Z)-allyl alcohols, (E)-alpha-phenyl-alpha,beta-unsaturated aldehydes and alpha-aryl acetophenones

机译：α-苯基硒基β-取代的苯乙烯的合成和反应性。（Z）-烯丙醇，（E）-α-苯基-α，β-不饱和醛和α-芳基苯乙酮的制备

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A new and efficient method was developed to prepare alpha-phenylseleno-beta-substituted styrenes by reaction of diethyl alpha-phenylseleno benzy1phosphonate with NaH and aldehydes. Selenium-lithium exchange by reaction with n-BuLi yielded the vinyl lithium species, which were captured with several electrophiles, like aldehydes and DMF, affording exclusively (Z)-allyl alcohols, and (E)-alpha-phenyl-alpha-beta-unsaturated aldehydes, respectively in good yields. The hydrolysis of the vinyl selenides in presence of TiCl4 allowed the corresponding alpha-aryl acetophenones.

机译：通过使二乙基α-苯基硒基苯磺酸膦酸酯与NaH和醛反应，开发了一种新的高效方法来制备α-苯基硒基β-取代的苯乙烯。通过与n-BuLi反应进行硒-锂交换，得到乙烯基锂物质，该乙烯基锂物质被数种亲电子试剂（如醛和DMF）捕获，仅提供（Z）-烯丙基醇和（E）-α-苯基-α-β-不饱和醛分别以良好的产率。在TiCl4存在下，乙烯基硒化物的水解得到相应的α-芳基苯乙酮。

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《Journal of the Brazilian Chemical Society》 |2006年第5期|共8页
作者
Lenardao EJ; Cella R; Jacob RG; da Silva TB; Perin G;
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正文语种 eng
中图分类化学;
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Horner-Wittig reactions; vinyl selenides; transmetallation; alpha; beta-unsaturated aldehydes; Z-allyl alcohols; SOLVENT-FREE CONDITIONS; VINYLIC SELENIDES; ALPHA-PHENYLSELENO-ALPHA; BETA-UNSATURATED ESTERS; KETENE PHENYLTELLUROACETALS; YLIDATION REACTION; ORGANIC-SYNTHESIS; ALLYLIC ALCOHOLS; TELLURIDES; ROUTE; PHENYLSELENOACRYLONITRILES;

机译：Horner-Wittig反应;乙烯基硒化物;金属间转移反应;α;β-不饱和醛;Z-烯丙基醇;无溶剂条件;乙烯基硒化物;α-苯并硒基-α-羟基苯丙酸酯;烯丙醇;碲;路线;苯酚丙烯腈;

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1. Synthesis and reactivity of alpha-phenylseleno-beta-substituted styrenes. Preparation of (Z)-allyl alcohols, (E)-alpha-phenyl-alpha,beta-unsaturated aldehydes and alpha-aryl acetophenones [J] . Lenardao EJ, Cella R, Jacob RG, Journal of the Brazilian Chemical Society . 2006,第5期

机译：α-苯基硒基β-取代的苯乙烯的合成和反应性。（Z）-烯丙醇，（E）-α-苯基-α，β-不饱和醛和α-芳基苯乙酮的制备
2. GRIGNARD ADDITIONS TO ALPHA,BETA-UNSATURATED DIOXOLANONES - PREPARATION OF CHIRAL ALLYLIC ALCOHOLS AND PROTECTED ALPHA-HYDROXY ALDEHYDES [J] . Heckmann B., Bhatt RK., Falck JR., Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1996,第9期

机译：粗大的阿尔法，不饱和的二氧戊环酮的添加物-手性烯醇和受保护的羟醛的制备
3. Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction [J] . Horino Yoshikazu, Aimono Ataru, Minoshima Naoki, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第31期

机译：通过钯催化的三组分反应，由3-（频哪醇硼硼基）烯丙基醇，醛和三有机硼烷轻松合成（Z）-反均丙醇
4. Ru/CeO2-Catalyzed Allyl Transfer Reaction of Homoallyl Alcohols to Aldehydes via C-C Bond Cleavage [C] . Hiroki Miura, Saburo Hosokawa, Teruyuki Kondo Symposium on Organometallic Chemistry . 2008

机译：Ru / CeO 2催化通过C-C键切割将Homoall醇的烯丙基转移反应转化为醛
5. I. Chemoselective catalytic hydrogenation of alpha, beta-unsaturated aldehydes and ketones using soluble copper(I) hydrides II. Free radical alkylation of titanium(III) allyl and propargyl complexes. [D] . Chen, Jianxian. 1999

机译：I.使用可溶的氢化铜（I）对α，β-不饱和醛和酮进行化学选择性催化氢化。钛（III）烯丙基和炔丙基复合物的自由基烷基化。
6. Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate [O] . In Su Kim, Ming-Yu Ngai, Michael J. Krische -1

机译：使用乙酸烯丙酯作为烯丙基金属替代物从醇或醛氧化水平对映选择性铱催化的羰基烯丙基化
7. Silyl Nitronates in Organic Synthesis. Silylation of Secondary Nitro Compounds. Preparation of Nitroso Compounds and alpha,beta-Unsaturated Aldehydes. [O] . Somir K. Mukerji, Kurt B. G. Torssell, Christina Ullenius, 1981

机译：含有有机合成中的甲硅烷基亚硝酸盐。仲硝基化合物的甲硅烷基化。制备亚硝基化合物和α，β-不饱和醛。
8. 9-Borabicyclo(3.3.1)nonane as a Highly Selective Reducing Agent for the Facile Conversion of alpha, beta-Unsaturated Aldehydes and Ketones to the Corresponding Allylic Alcohols in the Presence of Other Functional Groups. [R] . Krishnamurthy, S., Brown, H. C. 1975

机译：9-Borabicyclo（3.3.1）壬烷作为高选择性还原剂，用于在其他官能团存在下将α，β-不饱和醛和酮轻易转化为相应的烯丙醇。

Synthesis and reactivity of alpha-phenylseleno-beta-substituted styrenes. Preparation of (Z)-allyl alcohols, (E)-alpha-phenyl-alpha,beta-unsaturated aldehydes and alpha-aryl acetophenones

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