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Title: Stereoselective C-X and regioselective C-H activation to, and selective C(sp)-C(sp) reductive elimination from, platinum compounds with thiophene-derived ligands
Authors:
; ; ; ; ; ; ;
Award ID(s):
1665435
Publication Date:
NSF-PAR ID:
10186572
Journal Name:
Tetrahedron Letters
Volume:
60
Issue:
43
Page Range or eLocation-ID:
151156
ISSN:
0040-4039
Sponsoring Org:
National Science Foundation
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  1. A unique C(sp 3 )–H/C(sp 3 )–H dehydrocoupling of N -benzylimines with saturated heterocycles is described. Using super electron donor (SED) 2-azaallyl anions and aryl iodides as electron acceptors, single-electron-transfer (SET) generates an aryl radical. Hydrogen atom transfer (HAT) from saturated heterocycles or toluenes to the aryl radical generates alkyl radicals or benzylic radicals, respectively. The newly formed alkyl radicals and benzylic radicals couple with the 2-azaallyl radicals with formation of new C–C bonds. Experimental evidence supports the key hydrogen-abstraction by the aryl radical, which determines the chemoselectivity of the radical–radical coupling reaction. It is noteworthy that this procedure avoids the use of traditional strong oxidants and transition metals.