Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

被引：84

作者：

Daw, Prosenjit ^{[1
]}

Ben-David, Yehoshoa ^{[1
]}

Milstein, David ^{[1
]}

机构：

[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 38期

基金：

欧洲研究理事会;

关键词：

SECONDARY ALCOHOLS; FUNCTIONALIZED PYRIDINES; SELECTIVE SYNTHESIS; AROMATIC DIAMINES; DIRECT AMINATION; PRIMARY AMINES; PYRAZINES; PYRROLES; WATER; MULTIALKYLATION;

D O I：

10.1021/jacs.8b08385

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.

引用

页码：11931 / 11934

页数：4

共 45 条

[1] Alkyl pyrazine synthesis via an open heated bath with variable sugars, ammonia, and various amino acids [J].

Ara, Katayoun Mahdavi ;

Taylor, Larry T. ;

Ashraf-Khorassani, Mehdi ;

Coleman, William M. .

JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 2017, 97 (07) :2263-2270

[2] Direct Synthesis of Secondary Amines From Alcohols and Ammonia Catalyzed by a Ruthenium Pincer Complex [J].

Balaraman, Ekambaram ;

Srimani, Dipankar ;

Diskin-Posner, Yael ;

Milstein, David .

CATALYSIS LETTERS, 2015, 145 (01) :139-144

[3] Utilization of Common Ligands for the Ruthenium-Catalyzed Amination of Alcohols [J].

Baumann, Wolfgang ;

Spannenberg, Anke ;

Pfeffer, Jan ;

Haas, Thomas ;

Koeckritz, Angela ;

Martin, Andreas ;

Deutsch, Jens .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (52) :17702-17706

[4] New highlights in the synthesis and reactivity of 1,4-dihydropyrazine derivatives [J].

Chaignaud, Mathilde ;

Gillaizeau, Isabelle ;

Ouhamou, Nouara ;

Coudert, Gerard .

TETRAHEDRON, 2008, 64 (35) :8059-8066

[5] Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes [J].

Daw, Prosenjit ;

Kumar, Amit ;

Espinosa-Jalapa, Noel Angel ;

Diskin-Posner, Yael ;

Ben-David, Yehoshoa ;

Milstein, David .

ACS CATALYSIS, 2018, 8 (09) :7734-7741

[6] Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt [J].

Daw, Prosenjit ;

Ben-David, Yehoshoa ;

Milstein, David .

ACS CATALYSIS, 2017, 7 (11) :7456-7460

[7] Direct Synthesis of Pyrroles by Dehydrogenative Coupling of Diols and Amines Catalyzed by Cobalt Pincer Complexes [J].

Daw, Prosenjit ;

Chakraborty, Subrata ;

Garg, Jai Anand ;

Ben-David, Yehoshoa ;

Milstein, David .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (46) :14371-14375

[8] A Sustainable Multicomponent Pyrimidine Synthesis [J].

Deibl, Nicklas ;

Ament, Kevin ;

Kempe, Rhett .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (40) :12804-12807

[9] Novel pyrazines from the myxobacterium Chondromyces crocatus and marine bacteria [J].

Dickschat, JS ;

Reichenbach, H ;

Wagner-Döbler, I ;

Schulz, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4141-4153

[10]

Farberov MI., 1975, Chem. Heterocycl. Compd, V11, P1349, DOI [10.1007/BF00764521, DOI 10.1007/BF00764521]

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