Hui Li, Shaoying Ju, Ting Chen, Kun Ding, Weili Yan, Douglas W Stephan, Yile Wu
{"title":"2-二苯基膦-苯甲醛与13族路易斯酸的反应。","authors":"Hui Li, Shaoying Ju, Ting Chen, Kun Ding, Weili Yan, Douglas W Stephan, Yile Wu","doi":"10.1021/acs.inorgchem.5c01899","DOIUrl":null,"url":null,"abstract":"<p><p>2-Diphenylphosphinobenzaldehyde <b>1</b> reacts with the group 13 Lewis acids to give simple phosphine adducts C<sub>6</sub>H<sub>4</sub>P(C(O)H)(Ph)<sub>2</sub>InX<sub>3</sub>; X = Br <b>2</b> and I <b>3</b>. In contrast, the Lewis acids GaCl<sub>3</sub>, AlCl<sub>3</sub>, E(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (E = B or Al), and ClAl(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> affect Lewis acid/phosphine addition to a carbonyl group, affording zwitterions with either the eight-membered ring products [(C<sub>6</sub>H<sub>4</sub>C(H)(OER<sub>3</sub>)P(Ph)<sub>2</sub>)]<sub>2</sub> ER<sub>3</sub> = Al(C<sub>6</sub>F<sub>5</sub>)<sub><b>3</b></sub> <b>4</b>, Al(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>Cl <b>5</b>, AlCl<sub>3</sub> <b>6</b>, or GaCl<sub>3</sub> <b>7</b> or the six-membered ring species (C<sub>6</sub>H<sub>4</sub>C(H)(OB(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>)P(Ph)<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>C(H)(O) P(Ph)<sub>2</sub>)) <b>8</b>. These products derived from the frustrated Lewis pair additions to aldehyde fragments are fully characterized and described, and the differing reactivity is considered.</p>","PeriodicalId":40,"journal":{"name":"Inorganic Chemistry","volume":" ","pages":"14524-14530"},"PeriodicalIF":4.3000,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Reactions of 2-Diphenylphosphino-benzaldehyde with Group 13 Lewis Acids.\",\"authors\":\"Hui Li, Shaoying Ju, Ting Chen, Kun Ding, Weili Yan, Douglas W Stephan, Yile Wu\",\"doi\":\"10.1021/acs.inorgchem.5c01899\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>2-Diphenylphosphinobenzaldehyde <b>1</b> reacts with the group 13 Lewis acids to give simple phosphine adducts C<sub>6</sub>H<sub>4</sub>P(C(O)H)(Ph)<sub>2</sub>InX<sub>3</sub>; X = Br <b>2</b> and I <b>3</b>. In contrast, the Lewis acids GaCl<sub>3</sub>, AlCl<sub>3</sub>, E(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (E = B or Al), and ClAl(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> affect Lewis acid/phosphine addition to a carbonyl group, affording zwitterions with either the eight-membered ring products [(C<sub>6</sub>H<sub>4</sub>C(H)(OER<sub>3</sub>)P(Ph)<sub>2</sub>)]<sub>2</sub> ER<sub>3</sub> = Al(C<sub>6</sub>F<sub>5</sub>)<sub><b>3</b></sub> <b>4</b>, Al(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>Cl <b>5</b>, AlCl<sub>3</sub> <b>6</b>, or GaCl<sub>3</sub> <b>7</b> or the six-membered ring species (C<sub>6</sub>H<sub>4</sub>C(H)(OB(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>)P(Ph)<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>C(H)(O) P(Ph)<sub>2</sub>)) <b>8</b>. These products derived from the frustrated Lewis pair additions to aldehyde fragments are fully characterized and described, and the differing reactivity is considered.</p>\",\"PeriodicalId\":40,\"journal\":{\"name\":\"Inorganic Chemistry\",\"volume\":\" \",\"pages\":\"14524-14530\"},\"PeriodicalIF\":4.3000,\"publicationDate\":\"2025-07-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Inorganic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.inorgchem.5c01899\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/7/4 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Inorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.inorgchem.5c01899","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/7/4 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Reactions of 2-Diphenylphosphino-benzaldehyde with Group 13 Lewis Acids.
2-Diphenylphosphinobenzaldehyde 1 reacts with the group 13 Lewis acids to give simple phosphine adducts C6H4P(C(O)H)(Ph)2InX3; X = Br 2 and I 3. In contrast, the Lewis acids GaCl3, AlCl3, E(C6F5)3 (E = B or Al), and ClAl(C6F5)2 affect Lewis acid/phosphine addition to a carbonyl group, affording zwitterions with either the eight-membered ring products [(C6H4C(H)(OER3)P(Ph)2)]2 ER3 = Al(C6F5)34, Al(C6F5)2Cl 5, AlCl36, or GaCl37 or the six-membered ring species (C6H4C(H)(OB(C6F5)3)P(Ph)2(C6H4C(H)(O) P(Ph)2)) 8. These products derived from the frustrated Lewis pair additions to aldehyde fragments are fully characterized and described, and the differing reactivity is considered.
期刊介绍:
Inorganic Chemistry publishes fundamental studies in all phases of inorganic chemistry. Coverage includes experimental and theoretical reports on quantitative studies of structure and thermodynamics, kinetics, mechanisms of inorganic reactions, bioinorganic chemistry, and relevant aspects of organometallic chemistry, solid-state phenomena, and chemical bonding theory. Emphasis is placed on the synthesis, structure, thermodynamics, reactivity, spectroscopy, and bonding properties of significant new and known compounds.