N, N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki− Miyaura Cross-Coupling Partner

A Antoft-Finch, T Blackburn…

Index: Antoft-Finch, Aurora; Blackburn, Tom; Snieckus, Victor Journal of the American Chemical Society, 2009 , vol. 131, # 49 p. 17750 - 17752

Full Text: HTML

Citation Number: 162

Abstract

The first Suzuki− Miyaura cross-coupling of an aryl O-carbamate, a versatile and powerful directed metalation group (DMG) in directed ortho metalation (D o M) chemistry, is described using the inexpensive, bench-stable catalyst NiCl2 (PCy3) 2. Broad synthetic scope and good efficiency are demonstrated for aryl and heteroaryl O-carbamates. The role of water and hydrolysis equilibrium between free boronic acid and boroxine was established to be ...

~70%

~82%

~56%

~70%

~69%

~51%

~36%

~84%

~82%

~31%

~79%

~63%

~87%

~27%

Facile synthesis of 3-arylpyridine derivatives by palladacyc...

[Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie Tetrahedron, 2013 , vol. 69, # 2 p. 902 - 909]

Palladium nanoparticles on graphite oxide: A recyclable cata...

[Santra, Subhankar; Hota, Pradip Kumar; Bhattacharyya, Rangeet; Bera, Parthasarathi; Ghosh, Prasenjit; Mandal, Swadhin K. ACS Catalysis, 2013 , vol. 3, # 12 p. 2776 - 2789]

Highly efficient cyclopalladated ferrocenylimine catalyst fo...

[Zhang, Jinli; Zhao, Liang; Song, Maoping; Mak, Thomas C.W.; Wu, Yangjie Journal of Organometallic Chemistry, 2006 , vol. 691, # 6 p. 1301 - 1306]

Efficient Diphosphane??Based Catalyst for the Palladium??Cat...

[Fu, Xing-Li; Wu, Lei-Lei; Fu, Hai-Yan; Chen, Hua; Li, Rui-Xiang European Journal of Organic Chemistry, 2009 , # 13 p. 2051 - 2054]

Palladium-catalyzed, direct boronic acid synthesis from aryl...

[Molander, Gary A.; Trice, Sarah L. J.; Dreher, Spencer D. Journal of the American Chemical Society, 2010 , vol. 132, # 50 p. 17701 - 17703]