Cross Coupling between sp3-Carbon and sp3-Carbon Using a Diborylmethane Derivative at Room Temperature

…, T Ohkubo, T Ishioka, T Shibata

Index: Endo, Kohei; Ohkubo, Takahiro; Ishioka, Takafumi; Shibata, Takanori Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4826 - 4831

Full Text: HTML

Citation Number: 39

Abstract

A novel example of the Suzuki–Miyaura cross-coupling reaction between sp3-carbon and sp3-carbon is described. The reaction of a diborylmethane derivative with allyl halides or benzyl halides proceeded efficiently in the presence of appropriate Pd-catalysts at room temperature. The present approaches provide functionalized homoallylboronates and alkylboronates with excellent regio-and chemoselectivities.

Related Articles:

Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron Reagents to C− C Double Bonds

[Cano, Rafael; Ramon, Diego J.; Yus, Miguel Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3458 - 3460]

Regio-and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane

[Crudden, Cathleen M.; Hleba, Yonek B.; Chen, Austin C. Journal of the American Chemical Society, 2004 , vol. 126, # 30 p. 9200 - 9201]

Rh (I)-catalyzed borylation of primary alkyl chlorides

[Gong, Tian-Jun; Jiang, Yuan-Ye; Fu, Yao Chinese Chemical Letters, 2014 , vol. 25, # 3 p. 397 - 400]

Alkylboronic Esters from Copper??Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides

[Yang, Chu-Ting; Zhang, Zhen-Qi; Tajuddin, Hazmi; Wu, Chen-Cheng; Liang, Jun; Liu, Jing-Hui; Fu, Yao; Czyzewska, Maria; Steel, Patrick G.; Marder, Todd B.; Liu, Lei Angewandte Chemie - International Edition, 2012 , vol. 51, # 2 p. 528 - 532]

Di (isopropylprenyl) borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids

[Kalinin, Alexey V.; Scherer, Stefan; Snieckus, Victor Angewandte Chemie - International Edition, 2003 , vol. 42, # 29 p. 3399 - 3404]

More Articles...