Cu(OAc)2-Catalysed Oxidative Dual C-H/N-H Activation of Terminal Alkynes and N-Deprotected Sulfonimidamides: An Easy Access to N-Alkynylated Sulfonimidamides
We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The reaction leads to hitherto unknown N‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised N‐alkynylated sulfonimidamides cou...
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| Published in | European journal of organic chemistry Vol. 2015; no. 13; pp. 2861 - 2867 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.05.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Abstract | We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The reaction leads to hitherto unknown N‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised N‐alkynylated sulfonimidamides could undergo silica‐gel‐mediated hydrolysis to give the corresponding N‐acyl‐sulfonimidamides, as well as borane–dimethyl sulfide‐mediated reduction to give the corresponding N‐alkylated sulfonimidamides.
N‐Alkynylated sulfonimidamides have been synthesised through the CuII‐catalysed N–H/C–H activation reaction of N‐deprotected sulfonimidamides and terminal alkynes. The resulting N‐alkynylated sulfonimidamides react with SiO2 or BH3·SMe2 to give the corresponding carbonyl or alkyl derivative, respectively. |
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| AbstractList | Abstract
We report a mild and efficient Cu(OAc)
2
‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and
N
‐deprotected sulfonimidamides. The reaction leads to hitherto unknown
N
‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised
N
‐alkynylated sulfonimidamides could undergo silica‐gel‐mediated hydrolysis to give the corresponding
N
‐acyl‐sulfonimidamides, as well as borane–dimethyl sulfide‐mediated reduction to give the corresponding
N
‐alkylated sulfonimidamides. We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The reaction leads to hitherto unknown N‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised N‐alkynylated sulfonimidamides could undergo silica‐gel‐mediated hydrolysis to give the corresponding N‐acyl‐sulfonimidamides, as well as borane–dimethyl sulfide‐mediated reduction to give the corresponding N‐alkylated sulfonimidamides. N‐Alkynylated sulfonimidamides have been synthesised through the CuII‐catalysed N–H/C–H activation reaction of N‐deprotected sulfonimidamides and terminal alkynes. The resulting N‐alkynylated sulfonimidamides react with SiO2 or BH3·SMe2 to give the corresponding carbonyl or alkyl derivative, respectively. We report a mild and efficient Cu(OAc)2-catalysed protocol for the oxidative C-N cross-coupling of terminal alkynes and N-deprotected sulfonimidamides. The reaction leads to hitherto unknown N-alkynylated sulfonimidamides. Furthermore, we found that the synthesised N-alkynylated sulfonimidamides could undergo silica-gel-mediated hydrolysis to give the corresponding N-acyl-sulfonimidamides, as well as borane-dimethyl sulfide-mediated reduction to give the corresponding N-alkylated sulfonimidamides. |
| Author | Arvidsson, Per I. Kruger, Hendrick G. Kota, Sudhakar Rao Nandi, Ganesh Chandra Govender, Thavendran Naicker, Tricia |
| Author_xml | – sequence: 1 givenname: Ganesh Chandra surname: Nandi fullname: Nandi, Ganesh Chandra organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx – sequence: 2 givenname: Sudhakar Rao surname: Kota fullname: Kota, Sudhakar Rao organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx – sequence: 3 givenname: Tricia surname: Naicker fullname: Naicker, Tricia organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx – sequence: 4 givenname: Thavendran surname: Govender fullname: Govender, Thavendran organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx – sequence: 5 givenname: Hendrick G. surname: Kruger fullname: Kruger, Hendrick G. organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx – sequence: 6 givenname: Per I. surname: Arvidsson fullname: Arvidsson, Per I. email: per.arvidsson@scilifelab.se organization: Catalysis and Peptide Research Unit, University of KwaZulu Natal, Durban, South Africa, http://cpru.ukzn.ac.za/Homepage.aspx |
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| Keywords | SULFOXIMINES ORGANIC-CHEMICALS Sulfonimidamides ARYLATION EFFICIENT SYNTHESIS AMIDATION BOND FORMATION C-H activation DIRECT AMINATION C-N coupling BENZOXAZOLES Synthetic methods ARYL Sulfur Copper Alkynes INSIGHTS |
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| Snippet | We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The... We report a mild and efficient Cu(OAc)(2)-catalysed protocol for the oxidative C-N cross-coupling of terminal alkynes and N-deprotected sulfonimidamides. The... Abstract We report a mild and efficient Cu(OAc) 2 ‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N ‐deprotected... We report a mild and efficient Cu(OAc)2-catalysed protocol for the oxidative C-N cross-coupling of terminal alkynes and N-deprotected sulfonimidamides. The... |
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| SubjectTerms | Alkynes C-H activation C-N coupling Chemistry Chemistry, Organic Copper Medicin och hälsovetenskap Physical Sciences Science & Technology Sulfonimidamides Sulfur Synthetic methods |
| Title | Cu(OAc)2-Catalysed Oxidative Dual C-H/N-H Activation of Terminal Alkynes and N-Deprotected Sulfonimidamides: An Easy Access to N-Alkynylated Sulfonimidamides |
| URI | https://api.istex.fr/ark:/67375/WNG-47PQLCT2-2/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.201500239 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000354213400010 https://www.proquest.com/docview/1674393989 http://kipublications.ki.se/Default.aspx?queryparsed=id:131220309 |
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