Stephen R Sardini1, Alison L Lambright1, Grace L Trammel1, Humair M Omer2, Peng Liu2, M Kevin Brown1. 1. Department of Chemistry , Indiana University , 800 East Kirkwood Avenue , Bloomington , Indiana 47405 , United States. 2. Department of Chemistry , University of Pittsburgh , 219 Parkman Avenue , Pittsburgh , Pennsylvania 15260 , United States.
Abstract
A method for the Ni-catalyzed arylboration of unactivated monosubstituted, 1,1-disubstituted, and trisubstituted alkenes is disclosed. The reaction is notable in that it converts highly substituted alkenes, aryl bromides, and diboron reagents to products that contain a quaternary carbon and a synthetically versatile carbon-boron bond with control of stereoselectivity and regioselectivity. In addition, the method is demonstrated to be useful for the synthesis of saturated nitrogen heterocycles, which are important motifs in pharmaceutical compounds. Finally, due to the unusual reactivity demonstrated, the mechanistic details of the reaction were studied with both computational and experimental techniques.
A method for the Ni-catalyzed arylboration of unactivated monosubstituted, n class="Chemical">1,1-disubstituted, and trisubstituted alkenes is disclosed. The reaction is notable in that it converts highly substituted alkenes, aryl bromides, and diboron reagents to products that contain a quaternary carbon and a synthetically versatile carbon-boron bond with control of stereoselectivity and regioselectivity. In addition, the method is demonstrated to be useful for the synthesis of saturated nitrogenheterocycles, which are important motifs in pharmaceutical compounds. Finally, due to the unusual reactivity demonstrated, the mechanistic details of the reaction were studied with both computational and experimental techniques.
Authors: Chu-Ting Yang; Zhen-Qi Zhang; Hazmi Tajuddin; Chen-Cheng Wu; Jun Liang; Jing-Hui Liu; Yao Fu; Maria Czyzewska; Patrick G Steel; Todd B Marder; Lei Liu Journal: Angew Chem Int Ed Engl Date: 2011-12-01 Impact factor: 15.336
Authors: Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle Journal: Angew Chem Int Ed Engl Date: 2019-10-08 Impact factor: 15.336