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 , Fabio G. Delolo , Jakob Norinder , Armin Börner , André L. Bogado , 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 , Fabio G. Delolo , Jakob Norinder , Armin Börner , André L. Bogado , 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}
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.
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.