钌配合物催化的氢甲酰化-加氢和氢甲酰化-乙酰化反应

IF 5.062
Claudia Rodrigues , Fabio G. Delolo , Jakob Norinder , Armin Börner , André L. Bogado , Alzir A. Batista
{"title":"钌配合物催化的氢甲酰化-加氢和氢甲酰化-乙酰化反应","authors":"Claudia Rodrigues ,&nbsp;Fabio G. Delolo ,&nbsp;Jakob Norinder ,&nbsp;Armin Börner ,&nbsp;André L. Bogado ,&nbsp;Alzir A. Batista","doi":"10.1016/j.molcata.2016.09.020","DOIUrl":null,"url":null,"abstract":"<div><p>In this work, the catalytic activity of ruthenium II and III complexes containing chloride, pyridine, phosphine and CO ligands was investigated in the hydroformylation – hydrogenation and hydroformylation – acetalization reactions. The complexes <em>mer-</em>[RuCl<sub>3</sub>(dppb)(H<sub>2</sub>O)]<strong>(1)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Vpy)]<strong>(2)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-<em>t</em>Bupy)]<strong>(3)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(py)]<strong>(4)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Phpy)]<strong>(5)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Mepy)]<strong>(6)</strong>, <em>cis-</em>[RuCl<sub>2</sub>(CO)<sub>2</sub>(dppb)]<strong>(7)</strong>, <em>trans-</em>[RuCl<sub>2</sub>(CO)<sub>2</sub>(dppb)]<strong>(8)</strong>, RuCl<sub>3</sub>·xH<sub>2</sub>O<strong>(9)</strong>, [RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>3</sub>]<strong>(10)</strong> and [RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>(dppb)]<strong>(11)</strong> were used as supplied or synthesized as previously described in the literature {Where PPh<sub>3</sub> <!-->=<!--> <!-->triphenylphosphine, dppb<!--> <!-->=<!--> <!-->1,4-bis(diphenylphosphino)butane, py<!--> <!-->=<!--> <!-->pyridine, 4-Mepy<!--> <!-->=<!--> <!-->4-methylpyridine, 4-Vpy<!--> <!-->=<!--> <!-->4-vinylpyridine, 4-<em>t</em>Bupy<!--> <!-->=<!--> <!-->4-<em>tert</em>-butylpyridine and 4-Phpy<!--> <!-->=<!--> <!-->4-phenylpyridine}. These complexes were used as a pre-catalysts in a hydroformylation catalytic system to produce C<img>C, C<img>O and C<img>O bonds, where 1-decene resulted in a formation of respective alcohol and dimethyl acetals. Several reactions were performed in order to find the best reaction conditions presenting the best conversion (64% after 24<!--> <!-->h). The 1-decene was also used as a substrate in two type tandem reactions labeled as: hydroformylation – hydrogenation (HH) and hydroformylation – acetalization (HA) reactions. The relationship between Ru – catalyst/substrate was 1:100, without free ligands or additives, in a controlled temperature and pressure. All the products of catalytic reactions HH and HA were analyzed by CG-FID with good yields.</p></div>","PeriodicalId":370,"journal":{"name":"Journal of Molecular Catalysis A: Chemical","volume":"426 ","pages":"Pages 586-592"},"PeriodicalIF":5.0620,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.molcata.2016.09.020","citationCount":"14","resultStr":"{\"title\":\"Hydroformylation-hydrogenation and hydroformylation-acetalization reactions catalyzed by ruthenium complexes\",\"authors\":\"Claudia Rodrigues ,&nbsp;Fabio G. Delolo ,&nbsp;Jakob Norinder ,&nbsp;Armin Börner ,&nbsp;André L. Bogado ,&nbsp;Alzir A. Batista\",\"doi\":\"10.1016/j.molcata.2016.09.020\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In this work, the catalytic activity of ruthenium II and III complexes containing chloride, pyridine, phosphine and CO ligands was investigated in the hydroformylation – hydrogenation and hydroformylation – acetalization reactions. The complexes <em>mer-</em>[RuCl<sub>3</sub>(dppb)(H<sub>2</sub>O)]<strong>(1)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Vpy)]<strong>(2)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-<em>t</em>Bupy)]<strong>(3)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(py)]<strong>(4)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Phpy)]<strong>(5)</strong>, <em>mer-</em>[RuCl<sub>3</sub>(dppb)(4-Mepy)]<strong>(6)</strong>, <em>cis-</em>[RuCl<sub>2</sub>(CO)<sub>2</sub>(dppb)]<strong>(7)</strong>, <em>trans-</em>[RuCl<sub>2</sub>(CO)<sub>2</sub>(dppb)]<strong>(8)</strong>, RuCl<sub>3</sub>·xH<sub>2</sub>O<strong>(9)</strong>, [RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>3</sub>]<strong>(10)</strong> and [RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>(dppb)]<strong>(11)</strong> were used as supplied or synthesized as previously described in the literature {Where PPh<sub>3</sub> <!-->=<!--> <!-->triphenylphosphine, dppb<!--> <!-->=<!--> <!-->1,4-bis(diphenylphosphino)butane, py<!--> <!-->=<!--> <!-->pyridine, 4-Mepy<!--> <!-->=<!--> <!-->4-methylpyridine, 4-Vpy<!--> <!-->=<!--> <!-->4-vinylpyridine, 4-<em>t</em>Bupy<!--> <!-->=<!--> <!-->4-<em>tert</em>-butylpyridine and 4-Phpy<!--> <!-->=<!--> <!-->4-phenylpyridine}. These complexes were used as a pre-catalysts in a hydroformylation catalytic system to produce C<img>C, C<img>O and C<img>O bonds, where 1-decene resulted in a formation of respective alcohol and dimethyl acetals. Several reactions were performed in order to find the best reaction conditions presenting the best conversion (64% after 24<!--> <!-->h). The 1-decene was also used as a substrate in two type tandem reactions labeled as: hydroformylation – hydrogenation (HH) and hydroformylation – acetalization (HA) reactions. The relationship between Ru – catalyst/substrate was 1:100, without free ligands or additives, in a controlled temperature and pressure. All the products of catalytic reactions HH and HA were analyzed by CG-FID with good yields.</p></div>\",\"PeriodicalId\":370,\"journal\":{\"name\":\"Journal of Molecular Catalysis A: Chemical\",\"volume\":\"426 \",\"pages\":\"Pages 586-592\"},\"PeriodicalIF\":5.0620,\"publicationDate\":\"2017-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.molcata.2016.09.020\",\"citationCount\":\"14\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Catalysis A: Chemical\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1381116916303922\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Catalysis A: Chemical","FirstCategoryId":"1","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1381116916303922","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 14

摘要

本文研究了含氯、吡啶、膦和CO配体的钌II和钌III配合物在氢甲酰化-加氢和氢甲酰化-乙酰化反应中的催化活性。配合物mer-[RuCl3(dppb)(H2O)](1)、mer-[RuCl3(dppb)(4- vpy)](2)、mer-[RuCl3(dppb)(4- tbupy)](3)、mer-[RuCl3(dppb)(4- phpy)](4)、mer-[RuCl3(dppb)(4- phpy)](5)、mer-[RuCl3(dppb)(4- mepy)](6)、顺式-[RuCl2(CO)2(dppb)](7)、反式-[RuCl2(CO)2(dppb)](8)、RuCl3·xH2O(9)、[RuCl2(PPh3)3](10)和[RuCl2(PPh3)2(dppb)](11)按照文献中先前的描述进行供应或合成{其中PPh3 =三苯基膦,dppb = 1,4-二苯基膦丁烷,py =吡啶,4-Mepy = 4-甲基吡啶,4-Vpy = 4-乙烯基吡啶,4-tBupy = 4-叔丁基吡啶和4-Phpy = 4-苯基吡啶。这些配合物在氢甲酰化催化体系中用作预催化剂,生成CC、CO和CO键,其中1-癸烯分别生成醇和二甲基缩醛。为了找到最佳的反应条件(24 h后转化率为64%),进行了多次反应。1-癸烯还作为底物进行了两种串联反应:氢甲酰化-加氢(HH)和氢甲酰化-乙酰化(HA)反应。在控制温度和压力的条件下,钌催化剂与底物的比例为1:100,无游离配体和添加剂。用gc - fid对HH和HA两种催化反应的产物进行了分析,收率均较高。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Hydroformylation-hydrogenation and hydroformylation-acetalization reactions catalyzed by ruthenium complexes

Hydroformylation-hydrogenation and hydroformylation-acetalization reactions catalyzed by ruthenium complexes

In this work, the catalytic activity of ruthenium II and III complexes containing chloride, pyridine, phosphine and CO ligands was investigated in the hydroformylation – hydrogenation and hydroformylation – acetalization reactions. The complexes mer-[RuCl3(dppb)(H2O)](1), mer-[RuCl3(dppb)(4-Vpy)](2), mer-[RuCl3(dppb)(4-tBupy)](3), mer-[RuCl3(dppb)(py)](4), mer-[RuCl3(dppb)(4-Phpy)](5), mer-[RuCl3(dppb)(4-Mepy)](6), cis-[RuCl2(CO)2(dppb)](7), trans-[RuCl2(CO)2(dppb)](8), RuCl3·xH2O(9), [RuCl2(PPh3)3](10) and [RuCl2(PPh3)2(dppb)](11) were used as supplied or synthesized as previously described in the literature {Where PPh3 = triphenylphosphine, dppb = 1,4-bis(diphenylphosphino)butane, py = pyridine, 4-Mepy = 4-methylpyridine, 4-Vpy = 4-vinylpyridine, 4-tBupy = 4-tert-butylpyridine and 4-Phpy = 4-phenylpyridine}. These complexes were used as a pre-catalysts in a hydroformylation catalytic system to produce CC, CO and CO bonds, where 1-decene resulted in a formation of respective alcohol and dimethyl acetals. Several reactions were performed in order to find the best reaction conditions presenting the best conversion (64% after 24 h). The 1-decene was also used as a substrate in two type tandem reactions labeled as: hydroformylation – hydrogenation (HH) and hydroformylation – acetalization (HA) reactions. The relationship between Ru – catalyst/substrate was 1:100, without free ligands or additives, in a controlled temperature and pressure. All the products of catalytic reactions HH and HA were analyzed by CG-FID with good yields.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
自引率
0.00%
发文量
0
审稿时长
2.8 months
期刊介绍: The Journal of Molecular Catalysis A: Chemical publishes original, rigorous, and scholarly full papers that examine the molecular and atomic aspects of catalytic activation and reaction mechanisms in homogeneous catalysis, heterogeneous catalysis (including supported organometallic catalysis), and computational catalysis.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信