A general catalytic β-C-H carbonylation of aliphatic amines to β-lactams
Methods for the synthesis and functionalization of amines are intrinsically important to a variety of chemical applications. We present a general carbon-hydrogen bond activation process that combines readily available aliphatic amines and the feedstock gas carbon monoxide to form synthetically versa...
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| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2016-11, Vol.354 (6314), p.851-857 |
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| container_end_page | 857 |
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| container_issue | 6314 |
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| container_title | Science (American Association for the Advancement of Science) |
| container_volume | 354 |
| creator | Willcox, Darren Chappell, Ben G. N. Hogg, Kirsten F. Calleja, Jonas Smalley, Adam P. Gaunt, Matthew J. |
| description | Methods for the synthesis and functionalization of amines are intrinsically important to a variety of chemical applications. We present a general carbon-hydrogen bond activation process that combines readily available aliphatic amines and the feedstock gas carbon monoxide to form synthetically versatile value-added amide products. The operationally straightforward palladium-catalyzed process exploits a distinct reaction pathway, wherein a sterically hindered carboxylate ligand orchestrates an amine attack on a palladium anhydride to transform aliphatic amines into β-lactams. The reaction is successful with a wide range of secondary amines and can be used as a late-stage functionalization tactic to deliver advanced, highly functionalized amine products of utility for pharmaceutical research and other areas. |
| doi_str_mv | 10.1126/science.aaf9621 |
| format | Article |
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The reaction is successful with a wide range of secondary amines and can be used as a late-stage functionalization tactic to deliver advanced, highly functionalized amine products of utility for pharmaceutical research and other areas.</description><subject>Activation</subject><subject>Aliphatic amines</subject><subject>Amines</subject><subject>Amines - chemistry</subject><subject>Anhydrides</subject><subject>beta-Lactams - chemical synthesis</subject><subject>Carbon - chemistry</subject><subject>Carbon Monoxide</subject><subject>Carboxylates</subject><subject>Catalysis</subject><subject>Chemical attack</subject><subject>Hydrogen Bonding</subject><subject>Palladium</subject><subject>Palladium - chemistry</subject><issn>0036-8075</issn><issn>1095-9203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0LtOwzAUBmALgWgpzEygjCxpfYsvI6qAgiqxwBydODakcuISu0NfiwfhmUjV0pnpSOf_zhl-hK4JnhJCxSyaxnbGTgGcFpScoDHBusg1xewUjTFmIldYFiN0EeMK4yHT7ByNqFSF0BiP0ct99mE724PPDCTw29SY7Oc7n-eLYdFXodt6SE3osuAy8M36E3YC2qazMUthZz2YBG28RGcOfLRXhzlB748Pb_NFvnx9ep7fL3PDNEu5cBSIobq2moHFhnNec6IclVRLV6u6roESIzQ1QlS6qirtsFaYKVlhJ4FN0N3-77oPXxsbU9k20VjvobNhE0uiBC8KpYn8B-VE6oIXaqCzPTV9iLG3rlz3TQv9tiS43HVdHrouD10PF7eH55uqtfXR_5U7gJs9WMUU-mPOuSQEU8p-AalXhrc</recordid><startdate>20161118</startdate><enddate>20161118</enddate><creator>Willcox, Darren</creator><creator>Chappell, Ben G. 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| identifier | ISSN: 0036-8075 |
| ispartof | Science (American Association for the Advancement of Science), 2016-11, Vol.354 (6314), p.851-857 |
| issn | 0036-8075 1095-9203 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1864558917 |
| source | American Association for the Advancement of Science; Jstor Complete Legacy; MEDLINE |
| subjects | Activation Aliphatic amines Amines Amines - chemistry Anhydrides beta-Lactams - chemical synthesis Carbon - chemistry Carbon Monoxide Carboxylates Catalysis Chemical attack Hydrogen Bonding Palladium Palladium - chemistry |
| title | A general catalytic β-C-H carbonylation of aliphatic amines to β-lactams |
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