Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2020-06-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00429/full |
| _version_ | 1828791521332166656 |
|---|---|
| author | Ramachandra Reddy Putta Simin Chun Simin Chun Seok Beom Lee Seok Beom Lee Dong-Chan Oh Dong-Chan Oh Suckchang Hong Suckchang Hong |
| author_facet | Ramachandra Reddy Putta Simin Chun Simin Chun Seok Beom Lee Seok Beom Lee Dong-Chan Oh Dong-Chan Oh Suckchang Hong Suckchang Hong |
| author_sort | Ramachandra Reddy Putta |
| collection | DOAJ |
| description | Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η4-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles. |
| first_indexed | 2024-12-12T02:52:23Z |
| format | Article |
| id | doaj.art-80fc7d7f71934c2f92a6d9e394e0ef37 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-12T02:52:23Z |
| publishDate | 2020-06-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-80fc7d7f71934c2f92a6d9e394e0ef372022-12-22T00:40:51ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-06-01810.3389/fchem.2020.00429544227Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted BenzimidazolesRamachandra Reddy Putta0Simin Chun1Simin Chun2Seok Beom Lee3Seok Beom Lee4Dong-Chan Oh5Dong-Chan Oh6Suckchang Hong7Suckchang Hong8BK21 PLUS Project, College of Pharmacy, Seoul National University, Seoul, South KoreaBK21 PLUS Project, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaBK21 PLUS Project, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaBK21 PLUS Project, College of Pharmacy, Seoul National University, Seoul, South KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, South KoreaBK21 PLUS Project, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaBenzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η4-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles.https://www.frontiersin.org/article/10.3389/fchem.2020.00429/fulliron catalysisdehydrogenative couplingborrowing hydrogenalcoholbenzimidazoles |
| spellingShingle | Ramachandra Reddy Putta Simin Chun Simin Chun Seok Beom Lee Seok Beom Lee Dong-Chan Oh Dong-Chan Oh Suckchang Hong Suckchang Hong Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles Frontiers in Chemistry iron catalysis dehydrogenative coupling borrowing hydrogen alcohol benzimidazoles |
| title | Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles |
| title_full | Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles |
| title_fullStr | Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles |
| title_full_unstemmed | Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles |
| title_short | Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles |
| title_sort | iron catalyzed acceptorless dehydrogenative coupling of alcohols with aromatic diamines selective synthesis of 1 2 disubstituted benzimidazoles |
| topic | iron catalysis dehydrogenative coupling borrowing hydrogen alcohol benzimidazoles |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00429/full |
| work_keys_str_mv | AT ramachandrareddyputta ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT siminchun ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT siminchun ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT seokbeomlee ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT seokbeomlee ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT dongchanoh ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT dongchanoh ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT suckchanghong ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles AT suckchanghong ironcatalyzedacceptorlessdehydrogenativecouplingofalcoholswitharomaticdiaminesselectivesynthesisof12disubstitutedbenzimidazoles |