Rhenium(I) eta(2)-coordinated furan complexes: Converting furan into a 1,3-carbon dipole

You F; Friedman LA; Bassett KC; Lin YQ; Sabat M; Harman WD

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Rhenium(I) eta(2)-coordinated furan complexes: Converting furan into a 1,3-carbon dipole

机译：hen（I）eta（2）配位的呋喃配合物：将呋喃转化为1,3-碳偶极子

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TpRe(CO)(MeIm)(eta(2)-2-methylfuran) (1; Tp = hydridotris(pyrazolyl)borate and MeIm = N-methylimidazole) and TpRe(CO)(MeIm)(eta(2)-2,5-dimethylfuran) (9) undergo Lewis acid promoted cyclopentannulation reactions with enones and enals to generate 3-acetylcyclopentene complexes. During the reaction, a rearrangement occurs such that the alpha- and beta-carbons of the enone or enal are incorporated into the new carbocycle. The reactions are completely regioselective. Yields vary from 26 to 78%, depending on reaction conditions. Diastereomer ratios vary from 50:50 to > 95:5. In a similar fashion, these furan complexes undergo reactions with aldehydes to form acetyldihydrofuran complexes, where a new dihydrofuran ring is generated from the aldehyde and C3-C5 of the original furan. These dihydrofuran complexes are readily converted into the corresponding trisubstituted furans via oxidative demetalation. Attempts to synthesize TpRe(CO)(MeIm)(eta(2)-2-methoxyfuran) for the synthesis of cyclopentene esters resulted in the formation of a novel rhenium carbene.

机译：TpRe（CO）（MeIm）（eta（2）-2-甲基呋喃）（1; Tp =氢化三（吡唑基）硼酸酯且MeIm = N-甲基咪唑）和TpRe（CO）（MeIm）（eta（2）-2，（5-二甲基呋喃）（9）与路易斯酸和烯醛进行路易斯酸促进的环戊环化反应，生成3-乙酰基环戊烯络合物。在反应过程中，发生重排，使得烯酮或烯醛的α-碳和β-碳被结合到新的碳环中。反应是完全区域选择性的。取决于反应条件，产率在26％至78％之间变化。非对映异构体比率从50:50到> 95：5。这些呋喃配合物以类似的方式与醛发生反应，形成乙酰基二氢呋喃配合物，在其中由原始呋喃的醛和C3-C5生成新的二氢呋喃环。这些二氢呋喃配合物容易通过氧化脱金属而转化为相应的三取代呋喃。尝试合成用于合成环戊烯酯的TpRe（CO）（MeIm）（eta（2）-2-甲氧基呋喃）导致了新型novel卡宾的形成。

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《Organometallics》 |2005年第12期|共10页
作者
You F; Friedman LA; Bassett KC; Lin YQ; Sabat M; Harman WD;
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正文语种 eng
中图分类有机化学;
关键词
COORDINATED FURANS; AROMATIC-MOLECULES; ANNULATION; CYCLIZATION; HYDRIDOTRIS(PYRAZOLYL)BORATE; CYCLOPENTANNULATION; CONSTRUCTION; DEAROMATIZATION; PRODUCTS; PYRIDINE;

机译：协调的呋喃;芳族分子;废除;循环;玻尿酸（吡唑基）硼酸盐;环戊烷;结构;脱氨化;产品;吡啶;

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1. Rhenium(I) eta(2)-coordinated furan complexes: Converting furan into a 1,3-carbon dipole [J] . You F, Friedman LA, Bassett KC, Organometallics . 2005,第12期

机译：hen（I）eta（2）配位的呋喃配合物：将呋喃转化为1,3-碳偶极子
2. {μ-5-[1,3-Bis(2,4,6-trimethylphenyl)-3H-imidazolium-2-yl]-2-(2-oxoethenyl-1κC1)furan-3-yl-2κC3}-μ-hydrido-bis(tetracarbonylrhenium) tetrahydrofuran 0.67-solvate [J] . Bezuidenhout D.I., Landman M., Liles D.C., Acta Crystallographica Section E: Crystallographic Communications . 2012,第3期

机译：{μ-5-[1,3-双（2,4,6-三甲基苯基）-3H-咪唑-2-基] -2-（2-氧乙烯基-1κC1）呋喃-3-基-2κC3}-μ-氢化双（四羰基hen）四氢呋喃0.67-溶剂化物
3. Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water [J] . Green chemistry . 2020,第4期

机译：使用负载型铼促进的水中的1,3-丙二醇至2,5-双（羟甲基）呋喃的选择性氢化5-羟甲基糠醛及其缩醛
4. Potential for Phytoremediation of Soil Contaminated with Petroleum Hydrocarbons, PAHs, PCBs, Dioxins/Furans, and Metals at the Former Energy Technology Engineering Center [C] . Matthew R. Poltorak, Yarrow Nelson, Michael Curto International Conference on Remediation of Chlorinated and Recalcitrant Compounds . 2014

机译：用石油烃，PAHS，PCB，二恶英/呋喃和金属污染土壤的植物修复，在前能源技术工程中心
5. PART I: STRUCTURE OF FURAN RADICAL CATION AND THE MECHANISM OF ITS REACTION WITH 1,3-BUTADIENE. PART II: THE UNUSUALLY SLOW LOSS OF A HYDROGEN ATOM IN UNIMOLECULAR DISSOCIATION. PART III: ION-MOLECULE REACTIONS OF UNSATURATED ALCOHOLS. [D] . PHONGBETCHARA, RUCHA. 1981

机译：第一部分：呋喃自由基的结构及其与1,3-丁二烯反应的机理。第二部分：分子解离中氢原子异常缓慢的丢失。第三部分：不饱和醇的离子-分子反应。
6. Crystal structures of fac-tricarbonylchlorido(66′-dihydroxy-22′-bipyridine)rhenium(I) tetrahydrofuran monosolvate and fac-bromidotricarbonyl(66′-dihydroxy-22′-bipyridine)manganese(I) tetrahydrofuran monosolvate [O] . Sheri Lense, Nicholas A. Piro, Scott W. Kassel, 2016

机译：fac-三羰基氯基（66-二羟基-22-联吡啶）r（I）四氢呋喃单溶剂化物和fac-溴二羰基（66-二羟基-22-联吡啶）锰（I）的晶体结构四氢呋喃单溶剂化物
7. {μ-5-[1,3-Bis(2,4,6-trimethylphenyl)-3H-imidazolium-2-yl]-2-(2-oxoethenyl-1κC 1)furan-3-yl-2κC 3}-μ-hydrido-bis(tetracarbonylrhenium) tetrahydrofuran 0.67-solvate [O] . Landman, Marilé, van Westhuizen, Belinda, Bezuidenhout, Daniela I., 2012

机译：{μ-5-[1,3-双（2,4,6-三甲基苯基）-3H-咪唑-2-基] -2-（2-氧乙烯基-1κC 1）呋喃-3-yl-2κC 3}-μ-氢-双（四羰基hen）四氢呋喃0.67-溶剂化物

Rhenium(I) eta(2)-coordinated furan complexes: Converting furan into a 1,3-carbon dipole

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