Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals

Peraka Swamy; Mameda Naresh; Marri Mahender Reddy; Kodumuri Srujana; Chevella Durgaiah; Sripadi Prabhakar; Nama Narender

首页> 外文期刊>RSC Advances >Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals

【24h】

Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals

机译：低碘酸催化的甲醇加入乙烯基的甲醇：抗Markovnikov甲基缩醛的合成

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A novel metal-free, catalytic geminal dimethoxylation of vinylarenes based on in situ generated HOI species from iodide salt and oxone is reported. The preliminary mechanistic investigations suggest that the key factor for achieving the anti-Markovnikov regioselectivity is the semipinacol rearrangement of an iodo functionalized intermediate, which is confirmed by an isotope labeling experiment. In addition, the reaction involves the de-iodination of a co-iodo intermediate via its oxidation to hypervalent iodine species rather than a common iodide abstraction by electrophiles. The HRESI-MS studies support the conversion of monovalent iodine containing intermediates to trivalent iodine intermediates during the catalytic conversion of aromatic alkenes into the corresponding terminal acetals.

机译：据报道，基于原位产生来自碘化盐和氧尼的原位产生的乙烯基的无金属的无金属催化宝氧化氧基化。初步机械调查表明，实现抗马洛维尼科夫地区的关键因素是碘官能化中间体的半碱醇重排，其通过同位素标记实验证实。此外，该反应涉及通过其氧化对高化碘物质而不是通过电子手机的共同碘化物脱碘。 HRESI-MS研究支持在芳族烯烃催化转化到相应的末端缩醛中的催化转化期间将含有单价碘的中间体转化为三价碘中间体。

著录项

来源
《RSC Advances》 |2015年第90期|共5页
作者
Peraka Swamy; Mameda Naresh; Marri Mahender Reddy; Kodumuri Srujana; Chevella Durgaiah; Sripadi Prabhakar; Nama Narender;
展开▼
作者单位

CSIR Indian Inst Chem Technol Acad Sci &

Innovat Res Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol Acad Sci &

Innovat Res Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol I&

PC Div Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol I&

PC Div Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol I&

PC Div Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol Acad Sci &

Innovat Res Hyderabad 500007 Telangana India;

CSIR Indian Inst Chem Technol Acad Sci &

Innovat Res Hyderabad 500007 Telangana India;

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词

相似文献

外文文献
中文文献
专利

1. Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals [J] . Peraka Swamy, Mameda Naresh, Marri Mahender Reddy, RSC Advances . 2015,第90期

机译：低碘酸催化的甲醇加入乙烯基的甲醇：抗Markovnikov甲基缩醛的合成
2. Stereoselective Anti-Markovnikov Geminal Diamination and Dioxygenation of Vinylarenes Mediated by the Bromonium Ion [J] . Balaji Pandur Venkatesan, Chandrasekaran Srinivasan European journal of organic chemistry . 2016,第14期

机译：溴离子介导的乙烯基芳烃的立体选择性抗马尔科夫尼科夫双金属化和双加氧反应
3. Synthesis of geminal bisperoxides by acid-catalyzed reaction of acetals and enol ethers with tert-butyl hydroperoxide [J] . Terentev AO, Kutkin AV, Troizky NA, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2005,第13期

机译：缩醛和烯醇醚与叔丁基过氧化氢的酸催化反应合成双双过氧化物
4. CHEMOSELECTIVE CATALYTIC CONVERSION OF GLYCEROL TO METHYL LACTATE IN METHANOL OVER Sn- β ZEOLITES PREPARED BY THREE SYNTHESIS METHODS [C] . Wenjie Dong, Yalei Zhang, Xuefei Zhou ACS National Meeting Exhibition . 2015

机译：通过三种合成方法制备的SN-β沸石在甲醇中甘油的化学选择性催化转化甲醇甲醇
5. Studies in the synthesis of bridged nitrogen heterocycles. I. Regioselectivity and stereoselectivity of Diels-Alder cycloadditions of 1,2-dihydropyridines with styrene and methyl vinyl ketone. II. A rapid and efficient synthetic route toward 5-substituted-2-azabicyclo[2.1.1]hexanes . [D] . Huang, Qiuli. 2004

机译：桥接氮杂环的合成研究。 I.1，2-二氢吡啶与苯乙烯和甲基乙烯基酮的Diels-Alder环加成反应的区域选择性和立体选择性。二。一种快速高效的合成方法，可替代5个取代的2-氮杂双环[2.1.1]己烷。
6. Lewis acid-catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates [O] . Vincent Tran, Thomas G. Minehan -1

机译：路易斯酸催化的ynol醚缩醛的分子内缩合。 alkoxycycloalkene羧酸盐的合成
7. Facile Regiocontrolled Three-Step Synthesis of Poly-Substituted Furans, Pyrroles, and Thiophenes: Consecutive Michael Addition of Methyl Cyanoacetate to α,β-Enone, CuI-Mediated Aerobic Oxidation, and Acid-Catalyzed Paal-Knorr Synthesis [O] . Se-Hee Kim, Jin-Woo Lim, Cheol-Hee Lim, 2012

机译：容易细胞的细胞控制三步合成聚取代的呋喃，吡咯和噻吩：连续迈克尔加入氰基乙酸甲酯至α，β-烯酮，豆介导的有氧氧化和酸催化的Paal-Knorr合成
8. Direct Polynitroaliphatic Alcohol Addition to Alkenes. 1. Synthesis of New 2-Fluoro-2,2-dinitroethyl Acetals and Ethers [R] . Cochoy, R. E., McGuire, R. R., Shackelford, S. A. 1990

机译：直接多元脂族醇加成烯烃。 1.新的2-氟-2,2-二硝基乙基缩醛和醚的合成

Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals

摘要

著录项

相似文献

相关主题

期刊订阅