Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 17
Submit an article Journal homepage
239
Views
7
CrossRef citations to date
0
Altmetric
Articles

Rh-catalyzed C–N coupling of N-sulfonyl-1,2,3-trizales with secondary amines for regioselective synthesis of phenylvinyl-1,2-diamines

Xinwei HeKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-1974-2464View further author information
ORCID Icon,
Yuhao WuKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
,
Tongtong ZhouKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
,
Youpeng ZuoKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
,
Mengqing XieKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
,
Ruxue LiKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
,
Jiahui DuanKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaView further author information
&
Yongjia ShangKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. ChinaORCID Iconhttps://orcid.org/0000-0001-9873-9150View further author information
ORCID Icon show all
Pages 2685-2697 | Received 26 Mar 2020, Published online: 07 Jul 2020
 
Sample our Physical Sciences journals, sign in here to start your FREE access for 14 days

Abstract

An efficient and operationally simple method for the preparation of phenylvinyl-1,2-diamines by the Rh(II)-catalyzed C–N coupling of 1-sulfonyl-1H-1,2,3-triazoles with secondary amines (e.g., N-aryl glycine esters, diarylamines or 1-phenyl-2-(p-tolylamino)ethanone) via the 1,3-insertion of Rh(II)-azavinyl carbenes into sp3 N-H bond process has been developed. The optimized conditions tolerate various functional groups and afford the diverse (Z)-phenylvinyl-1,2-diamines in good to excellent yields with high regioselectivity. The method was also successfully extended to the synthesis of functional tertiary amines having a Z configuration of the (1-aryl-2-(sulfonamido)vinyl) substituent and two aryl groups.

Graphical Abstract

Additional information

Funding

The work was partially supported by the National Natural Science Foundation of China (No. 21772001), the Anhui Provincial Natural Science Foundation [No. 1808085MB41].

Log in via your institution

Access through your institution

Log in to Taylor & Francis Online

Restore content access

Restore content access for purchases made as guest
Purchase options * Save for later

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.