Tags

Type your tag names separated by a space and hit enter

Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives.
Org Lett. 2016 Mar 18; 18(6):1426-9.OL

Abstract

An unprecedented approach for the synthesis of imine derivatives was achieved via a Pd(II)-catalyzed dearomatization reaction of N-aryl ureas with internal alkynes. The corresponding spirocyclic imine derivatives were obtained with 20 examples in good to excellent yields. Mechanistic investigation indicated that an interesting 1,3-palladium migration process led to the α-regioselective dearomatization when 2-naphthyl ureas were used as the substrates. Fused ring products could also be obtained to further prove this migration process.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Jiang P
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Xu Y
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Sun F
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Liu X
State Grid Jilin Province Electric Power Research Institute , 4433 Renmin Street, Changchun 130021, China.
Li F
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Yu R
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Li Y
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Wang Q
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China. State Grid Jilin Province Electric Power Research Institute , 4433 Renmin Street, Changchun 130021, China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26934378

Citation

Jiang, Pingping, et al. "Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: an Approach to Imine Derivatives." Organic Letters, vol. 18, no. 6, 2016, pp. 1426-9.
Jiang P, Xu Y, Sun F, et al. Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives. Org Lett. 2016;18(6):1426-9.
Jiang, P., Xu, Y., Sun, F., Liu, X., Li, F., Yu, R., Li, Y., & Wang, Q. (2016). Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives. Organic Letters, 18(6), 1426-9. https://doi.org/10.1021/acs.orglett.6b00363
Jiang P, et al. Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: an Approach to Imine Derivatives. Org Lett. 2016 Mar 18;18(6):1426-9. PubMed PMID: 26934378.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives. AU - Jiang,Pingping, AU - Xu,Yongbao, AU - Sun,Fuxing, AU - Liu,Xufei, AU - Li,Feng, AU - Yu,Renfu, AU - Li,Yang, AU - Wang,Qifeng, Y1 - 2016/03/02/ PY - 2016/3/3/entrez PY - 2016/3/5/pubmed PY - 2016/3/5/medline SP - 1426 EP - 9 JF - Organic letters JO - Org Lett VL - 18 IS - 6 N2 - An unprecedented approach for the synthesis of imine derivatives was achieved via a Pd(II)-catalyzed dearomatization reaction of N-aryl ureas with internal alkynes. The corresponding spirocyclic imine derivatives were obtained with 20 examples in good to excellent yields. Mechanistic investigation indicated that an interesting 1,3-palladium migration process led to the α-regioselective dearomatization when 2-naphthyl ureas were used as the substrates. Fused ring products could also be obtained to further prove this migration process. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26934378/Pd_II__Catalyzed_ortho_C_H_Olefination/Dearomatization_of_N_Aryl_Ureas:_An_Approach_to_Imine_Derivatives_ DB - PRIME DP - Unbound Medicine ER -
Coronavirus Guidelines
Latest evidence on COVID-19 from PubMed, WHO, CDC.
Visit free Relief Central.
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.