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1.发明授权Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof 有权钌络合物及其在酯，酰胺和衍生物的形成和/或氢化方法中的用途公开(公告)号：US09045381B2
公开(公告)日：2015-06-02
申请号：US13880328
申请日：2011-10-11
Applicant: David Milstein , Ekambaram Balaraman , Chidambaram Gunanathan , Boopathy Gnanaprakasam , Jing Zhang
Inventor： David Milstein , Ekambaram Balaraman , Chidambaram Gunanathan , Boopathy Gnanaprakasam , Jing Zhang
IPC: B01J31/18 , C07B41/08 , C07C29/136 , C07C29/149 , C07C29/17 , C07C41/16 , C07C45/00 , C07C51/23 , C07C67/00 , C07C67/03 , C07C209/62 , C07C213/00 , C07C231/02 , C07C231/10 , C07D207/08 , C07D213/38 , C07D241/08 , C07D241/12 , C07D295/023 , C07D307/14 , C07D307/33 , C07D307/83 , C07D309/30 , C07D487/14 , C07F9/58 , C07F15/00 , C08G69/00 , C07C51/02 , C07C51/295 , C07B41/02 , C07B41/12 , C07B43/06 , C07C209/00 , C07C213/02 , C07F9/6558 , C07K1/00
CPC classification number: C07K5/12 , B01J31/18 , B01J31/189 , B01J31/2404 , B01J31/2409 , B01J31/248 , B01J31/2485 , B01J2231/40 , B01J2231/49 , B01J2231/643 , B01J2231/763 , B01J2531/0244 , B01J2531/821 , C07B41/02 , C07B41/08 , C07B41/12 , C07B43/04 , C07B43/06 , C07C29/136 , C07C29/149 , C07C29/177 , C07C41/16 , C07C41/26 , C07C45/002 , C07C45/006 , C07C51/00 , C07C51/02 , C07C51/23 , C07C51/295 , C07C67/00 , C07C67/03 , C07C67/297 , C07C209/00 , C07C209/62 , C07C213/00 , C07C213/02 , C07C231/02 , C07C231/10 , C07C2601/08 , C07C2601/10 , C07C2601/14 , C07D207/06 , C07D207/08 , C07D211/12 , C07D213/38 , C07D241/08 , C07D241/12 , C07D295/023 , C07D295/027 , C07D295/185 , C07D305/06 , C07D307/14 , C07D307/33 , C07D307/44 , C07D307/52 , C07D307/83 , C07D309/30 , C07D487/14 , C07F9/58 , C07F9/65583 , C07F15/0046 , C07F15/0053 , C07K1/00 , C08G69/00 , Y02P20/52 , C07C233/05 , C07C235/06 , C07C233/07 , C07C235/16 , C07C235/14 , C07C235/10 , C07C211/27 , C07C211/07 , C07C211/35 , C07C211/46 , C07C211/10 , C07C215/28 , C07C217/58 , C07C69/14 , C07C69/24 , C07C31/125 , C07C31/12 , C07C49/78 , C07C49/04 , C07C49/10 , C07C49/08 , C07C49/403 , C07C31/205 , C07C31/202 , C07C31/04 , C07C31/08 , C07C33/20 , C07C33/22 , C07C31/1355 , C07C31/10 , C07C43/13 , C07C69/78 , C07C69/75 , C07C53/124 , C07C53/126 , C07C59/125 , C07C57/32 , C07C61/08 , C07C57/30 , C07C65/21 , C07C63/08 , C07C63/06
Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.
Abstract translation: 本发明涉及新的钌催化剂和相关的硼氢化物络合物，以及这种催化剂的用途，特别是（1）将酰胺（包括聚酰胺）氢化成醇和胺; （2）由醇与胺制备酰胺（包括通过使二醇和二胺反应和/或通过氨基醇的聚合反应制备聚酰胺（例如多肽）; （3）将酯氢化成醇（包括环酯（内酯）或环状二酯（二内酯）或聚酯）的氢化）; （4）将有机碳酸酯（包括聚碳酸酯）氢化成醇，并将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物氢化成醇和胺; （5）醇与酯的脱氢偶联; （6）将仲醇醇化成酮类; （7）酯的酰胺化（即从酯和胺合成酰胺）; （8）使用酯酰化醇; （9）将醇与水偶联以形成羧酸; 和（10）β-氨基醇脱氢形成吡嗪。 本发明还涉及某些吡啶钌催化剂的新用途。
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公开(公告)号：US20090112005A1
公开(公告)日：2009-04-30
申请号：US12260936
申请日：2008-10-29
Applicant: David MILSTEIN , Chidambaram Gunanathan , Yehoshua Ben-David
Inventor： David MILSTEIN , Chidambaram Gunanathan , Yehoshua Ben-David
IPC: C07C231/00 , C07D307/54
CPC classification number: C07C231/00 , C07C231/10 , C07D307/52 , C07C233/05
Abstract: The present invention provides a process for preparing amides, by reacting a primary amine and a primary alcohol in the presence of a Ruthenium catalyst, to generate the amide and molecular hydrogen. According to the process of the invention, primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. This reaction is catalyzed by a Ruthenium complex, which is preferably based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3. Use of diamines in the reaction leads to bis-amides, whereas with a mixed primary/secondary amine substrate, chemoselective acylation of the primary amine group occurs.
Abstract translation: 本发明提供了一种通过在钌催化剂存在下使伯胺和伯醇反应来制备酰胺以产生酰胺和分子氢的方法。 根据本发明的方法，伯胺通过等摩尔量的醇直接酰化，以高产率和高转化数产生酰胺和分子氢（仅副产物）。 该反应由钌络合物催化，钌络合物优选基于式A1的脱芳构化的PNN型配体或式A2或A3的前体。 在反应中使用二胺会导致双酰胺，而使用混合的伯胺/仲胺底物时，会发生伯胺基的化学选择性酰化。
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3.发明授权Use of ruthenium complexes for formation and/or hydrogenation of amides and related carboxylic acid derivatives 有权钌络合物用于酰胺和相关羧酸衍生物的形成和/或氢化的用途公开(公告)号：US09290441B2
公开(公告)日：2016-03-22
申请号：US13471037
申请日：2012-05-14
Applicant: David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David , Ekambaram Balaraman , Boopathy Gnanaprakasam , Jing Zhang
Inventor： David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David , Ekambaram Balaraman , Boopathy Gnanaprakasam , Jing Zhang
IPC: C07C231/00 , C07C209/50 , C07C213/00 , C07C231/02 , C07D307/52 , C08L79/02 , C07C67/03 , C07K1/02 , C07K1/10
CPC classification number: C07K5/12 , C07C29/136 , C07C45/002 , C07C51/235 , C07C67/03 , C07C67/28 , C07C67/39 , C07C209/50 , C07C213/00 , C07C231/00 , C07C231/02 , C07C2601/08 , C07C2601/14 , C07D241/12 , C07D295/185 , C07D307/52 , C07D487/14 , C07K1/02 , C07K1/10 , C08L79/02 , Y02P20/52 , C07C233/05 , C07C235/06 , C07C235/10 , C07C233/36 , C07C211/27 , C07C215/28 , C08L1/00 , C07C69/14 , C07C69/24 , C07C31/04 , C07C31/08 , C07C31/10 , C07C31/12
Abstract: A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.
Abstract translation: 在钌络合物的存在下通过伯胺和伯醇反应制备酰胺以产生酰胺和分子氢的方法。 伯胺通过等摩尔量的醇直接酰化，以高产率和高周转数产生酰胺和分子氢（仅副产物）。 还公开了将酰胺氢化成醇和胺的方法; 将有机碳酸酯氢化成醇; 将氨基甲酸酯或脲衍生物氢化成醇和胺; 酯化酰胺化; 使用酯酰化醇; 醇与水和碱偶联形成羧酸; β-氨基醇的脱氢形成吡嗪和环状二肽; 并将仲醇脱氢成酮。 这些反应由基于式A1的脱芳香族PNN型配体或式A2或A3的前体的钌络合物催化。
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Patent Agency Ranking
公开(公告)号：US08586742B2
公开(公告)日：2013-11-19
申请号：US13057989
申请日：2009-08-10
Applicant: David Milstein , Chidambaram Gunanathan
Inventor： David Milstein , Chidambaram Gunanathan
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
Abstract translation: 本发明提供了新颖的钌基催化剂，以及通过在这种催化剂存在下使伯醇和氨反应制备胺的方法，以产生胺和水。 根据本发明的方法，伯醇直接与氨反应，以高产率和高的周转数产生伯胺和水。 该反应由新的钌络合物催化，其优选由喹啉基或吖啶基的钳形配体组成。
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5.发明申请NOVEL RUTHENIUM COMPLEXES AND THEIR USES IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND DERIVATIVES THEREOF 有权新型氢氧化钠复合物及其用于形成和/或加氢酯，氨基和衍生物的方法中的用途公开(公告)号：US20130281664A1
公开(公告)日：2013-10-24
申请号：US13880328
申请日：2011-10-11
Applicant: David Milstein , Ekambaram Balaraman , Chidambaram Gunanathan , Boopathy Gnanaprakasam , Jing Zhang
Inventor： David Milstein , Ekambaram Balaraman , Chidambaram Gunanathan , Boopathy Gnanaprakasam , Jing Zhang
IPC: C07F15/00 , C07D241/12 , C07C45/00 , C07F9/6558 , C07D213/38 , C07B41/08 , C07C209/00 , C07C213/02 , C07B43/06 , C07K1/00 , C07B41/12 , C07C29/149 , C07B41/02
CPC classification number: C07K5/12 , B01J31/18 , B01J31/189 , B01J31/2404 , B01J31/2409 , B01J31/248 , B01J31/2485 , B01J2231/40 , B01J2231/49 , B01J2231/643 , B01J2231/763 , B01J2531/0244 , B01J2531/821 , C07B41/02 , C07B41/08 , C07B41/12 , C07B43/04 , C07B43/06 , C07C29/136 , C07C29/149 , C07C29/177 , C07C41/16 , C07C41/26 , C07C45/002 , C07C45/006 , C07C51/00 , C07C51/02 , C07C51/23 , C07C51/295 , C07C67/00 , C07C67/03 , C07C67/297 , C07C209/00 , C07C209/62 , C07C213/00 , C07C213/02 , C07C231/02 , C07C231/10 , C07C2601/08 , C07C2601/10 , C07C2601/14 , C07D207/06 , C07D207/08 , C07D211/12 , C07D213/38 , C07D241/08 , C07D241/12 , C07D295/023 , C07D295/027 , C07D295/185 , C07D305/06 , C07D307/14 , C07D307/33 , C07D307/44 , C07D307/52 , C07D307/83 , C07D309/30 , C07D487/14 , C07F9/58 , C07F9/65583 , C07F15/0046 , C07F15/0053 , C07K1/00 , C08G69/00 , Y02P20/52 , C07C233/05 , C07C235/06 , C07C233/07 , C07C235/16 , C07C235/14 , C07C235/10 , C07C211/27 , C07C211/07 , C07C211/35 , C07C211/46 , C07C211/10 , C07C215/28 , C07C217/58 , C07C69/14 , C07C69/24 , C07C31/125 , C07C31/12 , C07C49/78 , C07C49/04 , C07C49/10 , C07C49/08 , C07C49/403 , C07C31/205 , C07C31/202 , C07C31/04 , C07C31/08 , C07C33/20 , C07C33/22 , C07C31/1355 , C07C31/10 , C07C43/13 , C07C69/78 , C07C69/75 , C07C53/124 , C07C53/126 , C07C59/125 , C07C57/32 , C07C61/08 , C07C57/30 , C07C65/21 , C07C63/08 , C07C63/06
Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.
Abstract translation: 本发明涉及新的钌催化剂和相关的硼氢化物络合物，以及这种催化剂的用途，特别是（1）将酰胺（包括聚酰胺）氢化成醇和胺; （2）由醇与胺制备酰胺（包括通过使二醇和二胺反应和/或通过氨基醇的聚合反应制备聚酰胺（例如多肽）; （3）将酯氢化成醇（包括环酯（内酯）或环状二酯（二内酯）或聚酯）的氢化）; （4）将有机碳酸酯（包括聚碳酸酯）氢化成醇，并将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物氢化成醇和胺; （5）醇与酯的脱氢偶联; （6）将仲醇醇化成酮类; （7）酯的酰胺化（即从酯和胺合成酰胺）; （8）使用酯酰化醇; （9）将醇与水偶联以形成羧酸; 和（10）β-氨基醇脱氢形成吡嗪。 本发明还涉及某些吡啶钌催化剂的新用途。
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6.发明申请公开(公告)号：US20120253042A1
公开(公告)日：2012-10-04
申请号：US13471037
申请日：2012-05-14
Applicant: David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David , Ekambaram Balaraman , Boopathy Gnanaprakasam , Jing Zhang
Inventor： David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David , Ekambaram Balaraman , Boopathy Gnanaprakasam , Jing Zhang
IPC: C07C209/50 , C07C67/02 , C07D241/12 , C07K5/12
CPC classification number: C07K5/12 , C07C29/136 , C07C45/002 , C07C51/235 , C07C67/03 , C07C67/28 , C07C67/39 , C07C209/50 , C07C213/00 , C07C231/00 , C07C231/02 , C07C2601/08 , C07C2601/14 , C07D241/12 , C07D295/185 , C07D307/52 , C07D487/14 , C07K1/02 , C07K1/10 , C08L79/02 , Y02P20/52 , C07C233/05 , C07C235/06 , C07C235/10 , C07C233/36 , C07C211/27 , C07C215/28 , C08L1/00 , C07C69/14 , C07C69/24 , C07C31/04 , C07C31/08 , C07C31/10 , C07C31/12
Abstract: A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.
Abstract translation: 在钌络合物的存在下通过伯胺和伯醇反应制备酰胺以产生酰胺和分子氢的方法。 伯胺通过等摩尔量的醇直接酰化，以高产率和高周转数产生酰胺和分子氢（仅副产物）。 还公开了将酰胺氢化成醇和胺的方法; 将有机碳酸酯氢化成醇; 将氨基甲酸酯或脲衍生物氢化成醇和胺; 酯化酰胺化; 使用酯酰化醇; 醇与水和碱偶联形成羧酸; β-氨基醇的脱氢形成吡嗪和环状二肽; 并将仲醇脱氢成酮。 这些反应由基于式A1的脱芳香族PNN型配体或式A2或A3的前体的钌络合物催化。
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公开(公告)号：US08178723B2
公开(公告)日：2012-05-15
申请号：US12260936
申请日：2008-10-29
Applicant: David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David
Inventor： David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David
IPC: C07C231/10
CPC classification number: C07C231/00 , C07C231/10 , C07D307/52 , C07C233/05
Abstract: The present invention provides a process for preparing amides, by reacting a primary amine and a primary alcohol in the presence of a Ruthenium catalyst, to generate the amide and molecular hydrogen. According to the process of the invention, primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. This reaction is catalyzed by a Ruthenium complex, which is preferably based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3. Use of diamines in the reaction leads to bis-amides, whereas with a mixed primary/secondary amine substrate, chemoselective acylation of the primary amine group occurs.
Abstract translation: 本发明提供了一种通过在钌催化剂存在下使伯胺和伯醇反应来制备酰胺以产生酰胺和分子氢的方法。 根据本发明的方法，伯胺通过等摩尔量的醇直接酰化，以高产率和高转化数产生酰胺和分子氢（仅副产物）。 该反应由钌络合物催化，钌络合物优选基于式A1的脱芳构化的PNN型配体或式A2或A3的前体。 在反应中使用二胺会导致双酰胺，而使用混合的伯胺/仲胺底物时，会发生伯胺基的化学选择性酰化。
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公开(公告)号：US20110152525A1
公开(公告)日：2011-06-23
申请号：US13057989
申请日：2009-08-10
Applicant: David Milstein , Chidambaram Gunanathan
Inventor： David Milstein , Chidambaram Gunanathan
IPC: C07F15/00 , C07C209/16 , C07C213/02 , C07D213/38 , C07D307/52 , C07D305/06 , C07F9/64
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
Abstract translation: 本发明提供新型的钌基催化剂，以及通过在这种催化剂存在下使伯醇和氨反应制备胺的方法，以产生胺和水。 根据本发明的方法，伯醇直接与氨反应，以高产率和高的周转数产生伯胺和水。 该反应由新的钌络合物催化，其优选由喹啉基或吖啶基的钳形配体组成。
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