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Keywords:

  • amides;
  • dehydration;
  • homogeneous catalysis;
  • nitriles;
  • zinc

Abstract

In the present study, the zinc-catalyzed dehydration of a variety of amides with N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) as a dehydration reagent into the corresponding nitriles has been examined in detail. With the straightforward and commercially available zinc(II)triflate as the precatalyst and MSTFA, an excellent system has been established to afford nitriles in excellent yields and chemoselectivities. After investigation of reaction conditions and the scope and limitations, several efforts were carried out to understand the reaction mechanism.

Im Rahmen dieser Arbeit wird die Zink-katalysierte Dehydration von primären Amiden zu den entsprechenden Nitrilen mit Hilfe von N-Methyl-N-(trimethylsilyl)trifluoroacetamid (MSTFA) vorgestellt. Hierbei konnten exzellente Ausbeuten und Selektivitäten (>99 %) durch Anwendung von einfachen und kommerziell verfügbaren Zinksalzen beobachtet werden. Nach eingehender Untersuchung verschiedenster Reaktionsparameter wurden die hervorragenden Eigenschaften des Katalysatorsystems in der Dehydration zahlreicher primärer Amide gezeigt. Zum tieferen Verständnis der Reaktion wurden verschiedene mechanistische Experimente durchgeführt.

Featured Compounds

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  1. 1 - 50
Compound 2
Molecular Weight:199.2463
Molecular Formula:C6H12F3NOSi
InChIKey:MSPCIZMDDUQPGJ-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:199.2463
Molecular Formula:C6H12F3NOSi
InChIKey:MSPCIZMDDUQPGJ-UHFFFAOYSA-N
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Compound 1
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:KXDAEFPNCMNJSK-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Compound 10
Molecular Weight:189.1345
Molecular Formula:C8H6F3NO
InChIKey:WEJHBEDHLLBJFW-UHFFFAOYSA-N
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Compound 11
Molecular Weight:146.146
Molecular Formula:C8H6N2O
InChIKey:FUKWTMJZHKZKFA-UHFFFAOYSA-N
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Compound 19
Molecular Weight:137.202
Molecular Formula:C7H7NS
InChIKey:QIOZLISABUUKJY-UHFFFAOYSA-N
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Compound 3
Molecular Weight:139.127
Molecular Formula:C7H6FNO
InChIKey:VNDHYTGVCGVETQ-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:121.1118
Molecular Formula:C7H4FN
InChIKey:AEKVBBNGWBBYLL-UHFFFAOYSA-N
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Compound 4
Molecular Weight:155.582
Molecular Formula:C7H6ClNO
InChIKey:BLNVISNJTIRAHF-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:137.566
Molecular Formula:C7H4ClN
InChIKey:GJNGXPDXRVXSEH-UHFFFAOYSA-N
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Compound 5
Molecular Weight:200.033
Molecular Formula:C7H6BrNO
InChIKey:ZRWNRAJCPNLYAK-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:182.017
Molecular Formula:C7H4BrN
InChIKey:HQSCPPCMBMFJJN-UHFFFAOYSA-N
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Compound 6
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:UHBGYFCCKRAEHA-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:VCZNNAKNUVJVGX-UHFFFAOYSA-N
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Compound 7
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:WGRPQCFFBRDZFV-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:BOHCMQZJWOGWTA-UHFFFAOYSA-N
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Compound 8
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:XXUNIGZDNWWYED-UHFFFAOYSA-N
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Compound 8a
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:NWPNXBQSRGKSJB-UHFFFAOYSA-N
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Compound 9
Molecular Weight:151.1626
Molecular Formula:C8H9NO2
InChIKey:GUCPYIYFQVTFSI-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:133.1473
Molecular Formula:C8H7NO
InChIKey:XDJAAZYHCCRJOK-UHFFFAOYSA-N
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Compound 10a
Molecular Weight:171.1193
Molecular Formula:C8H4F3N
InChIKey:DRNJIKRLQJRKMM-UHFFFAOYSA-N
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Compound 11a
Molecular Weight:128.1308
Molecular Formula:C8H4N2
InChIKey:BHXFKXOIODIUJO-UHFFFAOYSA-N
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Compound 12
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:VIPMBJSGYWWHAO-UHFFFAOYSA-N
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Compound 12a
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:IIZURLNRIMKEDL-UHFFFAOYSA-N
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Compound 13
Molecular Weight:171.1953
Molecular Formula:C11H9NO
InChIKey:JVXXKQIRGQDWOJ-UHFFFAOYSA-N
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Compound 13a
Molecular Weight:153.18
Molecular Formula:C11H7N
InChIKey:AZKDTTQQTKDXLH-UHFFFAOYSA-N
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Compound 14
Molecular Weight:171.1953
Molecular Formula:C11H9NO
InChIKey:RMHJJUOPOWPRBP-UHFFFAOYSA-N
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Compound 14a
Molecular Weight:153.18
Molecular Formula:C11H7N
InChIKey:YJMNOKOLADGBKA-UHFFFAOYSA-N
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Compound 15
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:DFPAKSUCGFBDDF-UHFFFAOYSA-N
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Compound 15a
Molecular Weight:104.1094
Molecular Formula:C6H4N2
InChIKey:GZPHSAQLYPIAIN-UHFFFAOYSA-N
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Compound 16
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:IBBMAWULFFBRKK-UHFFFAOYSA-N
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Compound 16a
Molecular Weight:104.1094
Molecular Formula:C6H4N2
InChIKey:FFNVQNRYTPFDDP-UHFFFAOYSA-N
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Compound 17
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:LSBDFXRDZJMBSC-UHFFFAOYSA-N
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Compound 17a
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SUSQOBVLVYHIEX-UHFFFAOYSA-N
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Compound 18
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:CKBZJTAMRPPVSR-UHFFFAOYSA-N
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Compound 18a
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:FQFZASRJFRAEIH-UHFFFAOYSA-N
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Compound 19a
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Compound 21
Molecular Weight:127.0652
Molecular Formula:C3H4F3NO
InChIKey:IQNHBUQSOSYAJU-UHFFFAOYSA-N
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Compound 25
Molecular Weight:162.3775
Molecular Formula:C6H18OSi2
InChIKey:UQEAIHBTYFGYIE-UHFFFAOYSA-N
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Compound 27
Molecular Weight:90.1964
Molecular Formula:C3H10OSi
InChIKey:AAPLIUHOKVUFCC-UHFFFAOYSA-N
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Compound 30
Molecular Weight:211.3082
Molecular Formula:C10H14FNOSi
InChIKey:OQSKDJPUXHZZKX-UHFFFAOYSA-N
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Compound 29
Molecular Weight:283.4893
Molecular Formula:C13H22FNOSi2
InChIKey:NAPNINJVSGAQOC-FYWRMAATSA-N
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Compound 28
Molecular Weight:158.557
Molecular Formula:C7H4ClFO
InChIKey:CZKLEJHVLCMVQR-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:199.2463
Molecular Formula:C6H12F3NOSi
InChIKey:FYFRFEAOZNSIHX-BJMVGYQFSA-N
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Compound 33
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound 31
Molecular Weight:203.4294
Molecular Formula:C8H21NOSi2
InChIKey:VTACLVUOTMPORB-UHFFFAOYSA-N
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Compound 32
Molecular Weight:203.4294
Molecular Formula:C8H21NOSi2
InChIKey:SIOVKLKJSOKLIF-CMDGGOBGSA-N
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Compound 34
Molecular Weight:131.2483
Molecular Formula:C5H13NOSi
InChIKey:LWFWUJCJKPUZLV-UHFFFAOYSA-N
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Compound 36
Molecular Weight:131.2483
Molecular Formula:C5H13NOSi
InChIKey:RAZBQBDVZOHZPS-AATRIKPKSA-N
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