Phosphine‐Free NNN‐Manganese Complex Catalyzed α‐Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis
Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3233-3238 |
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| container_issue | 17 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Barman, Milan K. Jana, Akash Maji, Biplab |
| description | Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol. The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions. A range of ketones were efficiently diversified with a broad range of primary alcohols in good to excellent isolated yields. Remarkably, this catalyst could also be employed for the synthesis of quinoline derivatives using 2‐aminobenzyl alcohol as an alkylating agent. The later reaction is highly benign producing only hydrogen and water as byproducts. |
| doi_str_mv | 10.1002/adsc.201800380 |
| format | Article |
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The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions. A range of ketones were efficiently diversified with a broad range of primary alcohols in good to excellent isolated yields. Remarkably, this catalyst could also be employed for the synthesis of quinoline derivatives using 2‐aminobenzyl alcohol as an alkylating agent. 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The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions. A range of ketones were efficiently diversified with a broad range of primary alcohols in good to excellent isolated yields. Remarkably, this catalyst could also be employed for the synthesis of quinoline derivatives using 2‐aminobenzyl alcohol as an alkylating agent. The later reaction is highly benign producing only hydrogen and water as byproducts.</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>Alkylation</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Friedländer reaction</subject><subject>Hydrogen-autotransfer</subject><subject>Ketones</subject><subject>Manganese</subject><subject>Manganese catalysts</subject><subject>NNN-pincer</subject><subject>Quinoline</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQhyMEEn9XZkvMLWenceyxChQQUECFOXKTC0lx7WKngjAxMvIQvADPwM5D8CQEFZWR6X7D97vTfUGwS6FLAdi-yn3WZUAFQChgJdignEadHuVydZkjWA82vZ8A0FjE8UbwcllaPysrg1_PrwOHSIbDYRvPlblVBj2SxE5nGh9JomqlmyfMyed7C_T1XaNVXVlDbEFOsbYtTR6quiSXrpoq15C-zmxptSfK5GTgKsz1x5vJ0ZGreWWsbo-SUWPqEn3lt4O1QmmPO79zK7gZHF4nx52zi6OTpH_WyUIaQ0eMOWOqJ1kkZA48xKLHOISSZYxBHIGIIwSpeMwVFoLxCMaFjMeIuZAFizDcCvYWe2fO3s_R1-nEzp1pT6YMpOBh64-1VHdBZc5677BIZ4unUgrpj-30x3a6tN0W5KLwUGls_qHT_sEo-et-AyUhiOo</recordid><startdate>20180903</startdate><enddate>20180903</enddate><creator>Barman, Milan K.</creator><creator>Jana, Akash</creator><creator>Maji, Biplab</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20180903</creationdate><title>Phosphine‐Free NNN‐Manganese Complex Catalyzed α‐Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis</title><author>Barman, Milan K. ; Jana, Akash ; Maji, Biplab</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3170-8b622a492589d063ef4260392c220750875e09a676aef82650bf97beed89f25e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>Alkylation</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Friedländer reaction</topic><topic>Hydrogen-autotransfer</topic><topic>Ketones</topic><topic>Manganese</topic><topic>Manganese catalysts</topic><topic>NNN-pincer</topic><topic>Quinoline</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barman, Milan K.</creatorcontrib><creatorcontrib>Jana, Akash</creatorcontrib><creatorcontrib>Maji, Biplab</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barman, Milan K.</au><au>Jana, Akash</au><au>Maji, Biplab</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphine‐Free NNN‐Manganese Complex Catalyzed α‐Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-09-03</date><risdate>2018</risdate><volume>360</volume><issue>17</issue><spage>3233</spage><epage>3238</epage><pages>3233-3238</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol. 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| ispartof | Advanced synthesis & catalysis, 2018-09, Vol.360 (17), p.3233-3238 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohol Alcohols Alkylation Catalysis Chemical synthesis Friedländer reaction Hydrogen-autotransfer Ketones Manganese Manganese catalysts NNN-pincer Quinoline |
| title | Phosphine‐Free NNN‐Manganese Complex Catalyzed α‐Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis |
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