Tandem, Catalyst‐Free C‐C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite
Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C‐C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepar...
Saved in:
| Published in: | European journal of organic chemistry |
|---|---|
| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
19-11-2024
|
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C‐C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to create carbon backbones of organic molecules; however, it requires subsequent reduction and/or decarboxylation to achieve a product with a saturated carbon chain. Herein we report a convenient one‐step protocol for the reductive condensation between methyl cyanoacetate and aldehydes in the presence of stable, ecologically benign, cheap and available in bulk amounts sodium hypophosphite as a reductant. A description of both the reaction capabilities and limitations is given in this paper. |
|---|---|
| AbstractList | Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C‐C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to create carbon backbones of organic molecules; however, it requires subsequent reduction and/or decarboxylation to achieve a product with a saturated carbon chain. Herein we report a convenient one‐step protocol for the reductive condensation between methyl cyanoacetate and aldehydes in the presence of stable, ecologically benign, cheap and available in bulk amounts sodium hypophosphite as a reductant. A description of both the reaction capabilities and limitations is given in this paper. |
| Author | Chusov, Denis Boldyrev, Alexander Podyacheva, Evgeniya Korochantsev, Vasily Afanasyev, Oleg Fatkulin, Artemy |
| Author_xml | – sequence: 1 givenname: Vasily surname: Korochantsev fullname: Korochantsev, Vasily organization: A N Nesmeyanov Institute of Organoelement Compounds RAS: FGBUN Institut elementoorganiceskih soedinenij imeni A N Nesmeanova Rossijskoj akademii nauk Chemistry RUSSIAN FEDERATION – sequence: 2 givenname: Artemy surname: Fatkulin fullname: Fatkulin, Artemy organization: A N Nesmeyanov Institute of Organoelement Compounds RAS: FGBUN Institut elementoorganiceskih soedinenij imeni A N Nesmeanova Rossijskoj akademii nauk Chemistry RUSSIAN FEDERATION – sequence: 3 givenname: Evgeniya surname: Podyacheva fullname: Podyacheva, Evgeniya organization: A N Nesmeyanov Institute of Organoelement Compounds RAS: FGBUN Institut elementoorganiceskih soedinenij imeni A N Nesmeanova Rossijskoj akademii nauk Chemistry RUSSIAN FEDERATION – sequence: 4 givenname: Alexander surname: Boldyrev fullname: Boldyrev, Alexander organization: A N Nesmeyanov Institute of Organoelement Compounds RAS: FGBUN Institut elementoorganiceskih soedinenij imeni A N Nesmeanova Rossijskoj akademii nauk Chemistry RUSSIAN FEDERATION – sequence: 5 givenname: Oleg surname: Afanasyev fullname: Afanasyev, Oleg organization: A N Nesmeyanov Institute of Organoelement Compounds RAS: FGBUN Institut elementoorganiceskih soedinenij imeni A N Nesmeanova Rossijskoj akademii nauk Chemistry RUSSIAN FEDERATION – sequence: 6 givenname: Denis surname: Chusov fullname: Chusov, Denis organization: Institut èlementoorganičeskih soedinenij imeni A N Nesmeânova RAN Chemistry Vavilova St. 28 119991 Moscow RUSSIAN FEDERATION |
| BookMark | eNqVj7FOwzAURS3USrTQlfl9AAnPSRThEUVUXWBpBzbLSl5kV44d2UbIG5_AN_IlpBJiZ7rnDvdKZ8tWzjti7I5jyRGrBzr7vqywapBzfLxiG45CFNgKXC3c1E3BRf12zbYxnhFRtC3fsHRSbqDpHjqVlM0xfX9-7QMRdAt0cMwuaYomgh_h1aRgLEUYg5_gyQ6k87DU5QFeKOlsocvKedVTUongwyQNRz-Y9wkOefaz9nHWJtEtW4_KRtr95g0r98-n7lD0wccYaJRzMJMKWXKUFzd5cZN_bvW_Bz9Fn1x4 |
| ContentType | Journal Article |
| DBID | AAYXX CITATION |
| DOI | 10.1002/ejoc.202401108 |
| DatabaseName | CrossRef |
| DatabaseTitle | CrossRef |
| DatabaseTitleList | CrossRef |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1099-0690 |
| ExternalDocumentID | 10_1002_ejoc_202401108 |
| GroupedDBID | -~X .3N .GA 05W 0R~ 10A 1L6 1OC 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AABCJ AAESR AAEVG AAHHS AAMNL AANLZ AAONW AAXRX AAYXX AAZKR ABCQN ABCUV ABDBF ABEML ABIJN ABJNI ABLJU ABPVW ACAHQ ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACSCC ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFZJQ AHBTC AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BY8 CITATION CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EBS F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LITHE LOXES LP6 LP7 LUTES LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2P P2W P2X P4D Q.N Q11 QB0 QRW R.K ROL RWI RX1 SUPJJ TN5 UB1 UPT V2E W8V W99 WBFHL WBKPD WH7 WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XV2 ~IA ~WT |
| ID | FETCH-crossref_primary_10_1002_ejoc_2024011083 |
| ISSN | 1434-193X |
| IngestDate | Fri Nov 22 01:17:13 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Language | English |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-crossref_primary_10_1002_ejoc_2024011083 |
| ParticipantIDs | crossref_primary_10_1002_ejoc_202401108 |
| PublicationCentury | 2000 |
| PublicationDate | 2024-11-19 |
| PublicationDateYYYYMMDD | 2024-11-19 |
| PublicationDate_xml | – month: 11 year: 2024 text: 2024-11-19 day: 19 |
| PublicationDecade | 2020 |
| PublicationTitle | European journal of organic chemistry |
| PublicationYear | 2024 |
| SSID | ssj0009661 |
| Score | 4.9840865 |
| Snippet | Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C‐C single bonds is of primary importance in... |
| SourceID | crossref |
| SourceType | Aggregation Database |
| Title | Tandem, Catalyst‐Free C‐C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1Lb4JAEN6oPbSXps_0nT006YHSKvg8GqrxUmOih94IhSXSKksUTbj1J_Q39pd0hmUX7SOxh14IjrIg82VmGGa-IeS6xvxqxTMrumE0HMxWlXUI6h29Zfgtx6iBS2GYh-wNG_2n5kOn2ikU5Oy9XPavmgYZ6Bo7Z_-gbbUoCGAfdA5b0DpsN9M7ZoWnWXMfEo7Eqp6hO2NMs9RHSxsmIcR_GSVJP4hnYCLmouOkPfHYOPGYoHB-ZKDPiWYlTsgdFysUmcjgDrkXLKZaL4l4NObzCF9K_JrszwJfMUjK1Vw5a04ZfY7zu7AwB_401t868yCvNu068esiGy_fxgph9c2AewnyUi_TQLizhHsTJHmigU-8ZCZWVO08q8kOo4pdf5lJFfa5aoKslY4QBvclZOWUSEFMHf3mEQTDLHvhyFcJ4Qu2PeS-T77v_-ISVaGiIHU2bDzeVscXyZYBdg3NqmkOco7nuqDnldcoOULLxv36-VdioJVgZrRHdrOnENoW8NknBRYekG1LKuSQxAJGt1SC6OPtHeFDLdixqAIO5T6VwKEIHKqAQ2EFKoBDV4FDEThUAIeuAeeI3HU7I6uny8u2I8GFYv98g8xjUgp5yE4IrbhOy4VnI5_VG-Av2LPrI-UexI1mrd5s1k_JzYaLnm38y3Oyk4PngpTi2YJdkuLcW1ylGvsEvfh3KQ |
| link.rule.ids | 315,782,786,27933,27934 |
| linkProvider | Wiley-Blackwell |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Tandem%2C+Catalyst%E2%80%90Free+C%E2%80%90C+Synthesis+of+Nitriles+from+Aldehydes+and+Methyl+Cyanoacetate+with+Sodium+Hypophosphite&rft.jtitle=European+journal+of+organic+chemistry&rft.au=Korochantsev%2C+Vasily&rft.au=Fatkulin%2C+Artemy&rft.au=Podyacheva%2C+Evgeniya&rft.au=Boldyrev%2C+Alexander&rft.date=2024-11-19&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002%2Fejoc.202401108&rft.externalDBID=n%2Fa&rft.externalDocID=10_1002_ejoc_202401108 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1434-193X&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1434-193X&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1434-193X&client=summon |