Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 11
283
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

Selenium-Catalyzed Oxidative Carbonylation of Aniline and Alcohols to N-Phenylcarbamates

, &
Pages 1614-1624 | Received 02 Apr 2009, Published online: 06 May 2010
 

Abstract

A facile one-pot, phosgene-free synthesis of N-phenylcarbamates is demonstrated. Catalyzed by selenium, oxidative carbonylation of aniline with alcohols in the presence of carbon monoxide and oxygen affords the corresponding N-phenylcarbamates, mostly in fair to good yields. Selenium can be easily recovered because of its phase-transfer catalysis function.

ACKNOWLEDGMENTS

We sincerely acknowledge the financial supports from the Program for Innovative Research Team in University of Henan Province, China (2008IRTSTHN002) and the Education Department of Henan Province, China (2009B150013).

Notes

a Reaction conditions: aniline, 5 mmol; ethanol, 50 mmol; selenium, 0.25 mmol; triethylamine, 10 mmol; CO, 1.6 MPa; O2, 0.4 MPa; time, 6 h.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; ethanol, 50 mmol; selenium, 0.25 mmol; triethylamine, 10 mmol; CO, 1.6 MPa; O2, 0.4 MPa; temperature, 180 °C.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; ethanol, 50 mmol; selenium, 0.25 mmol; triethylamine, 10 mmol; temperature, 180 °C; time, 6 h.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; selenium, 0.25 mmol; triethylamine, 10 mmol; CO, 1.6 MPa; O2, 0.4 MPa; temperature, 180 °C; time, 6 h.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; ethanol, 50 mmol; selenium, 0.25 mmol; CO, 1.6 MPa; O2, 0.4 MPa; temperature, 180 °C; time, 6 h.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; ethanol, 50 mmol; triethylamine, 10 mmol; CO, 1.6 MPa; O2, 0.4 MPa; temperature, 180 °C; time, 6 h.

b Based on aniline.

c Isolated yield.

a Reaction conditions: aniline, 5 mmol; alcohol, 50 mmol; selenium, 0.25 mmol; triethylamine, 10 mmol; CO, 1.6 MPa; O2, 0.4 MPa; temperature, 180 °C; time, 6 h.

b Isolated yield.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.