Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA.
Published: March 2020
AI Article Synopsis
Article Abstract
A method for the regioselective 1,2-arylboration of 1,3-butadiene, a feedstock chemical, is reported. The reactions result in the formation of products that can be easily elaborated to other structures. The mechanistic details of this process are also discussed.
Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
We report herein a three-component 1,2-arylboration of alkenyl amines bearing a cleavable picolinamide directing group. With aryl halides as electrophiles and BPin as nucleophiles, a wide range of alkenes could be converted into valuable boryl-functionalized aliphatic amines. The reaction proceeds with high levels of chemo- and regiocontrol and exhibits high functional group tolerance.
Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biologically active molecules. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermolecular dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions.
A method for the regioselective 1,2-arylboration of 1,3-butadiene, a feedstock chemical, is reported. The reactions result in the formation of products that can be easily elaborated to other structures. The mechanistic details of this process are also discussed.
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.
A method for (hetero)arylboration of alkynes is presented. The reaction allows for the synthesis of densely functionalized tetrasubstituted alkenes with control of regioselectivity and diastereoselectivity. The conversion of the products to the corresponding α,α-bis(hetero)arylketones is also shown.
