Abstract
In the present Short Note, we report a synthesis for the title compound, N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide by reacting 2-methylbenzoyl chloride (or 2-methylbenzoic acid) with 1-aminoanthraquinone. The synthesized target compound was fully characterized by various spectroscopic methods (1H-NMR, 13C-NMR, IR, GC-MS). The importance of this compound lies its possession of an N,O-bidentate directing group, potentially suitable for metal-catalyzed C-H bond functionalization reactions.
Highlights
Functionalization of inert nonreactive C-H Bonds [1,2] has emerged as a powerful strategy for expedient chemical bonds
Directing groups have been developed as demonstrated by monondentate [5,6] and bidentate directing groups [7]
In continuation of our program [11,12] in the design of novel directing groups potentially applicable in metal-catalyzed C-H bond functionalization, we report a design-based benzamide bearing
Summary
Functionalization of inert nonreactive C-H Bonds [1,2] has emerged as a powerful strategy for expedient chemical bonds. Functionalization of C-H bonds could be environmentally benign approach and a green science. One approach to help provide regiocontrol is the use of groups that can direct the reaction to occur at a specific C-H bond. The key role of directing groups is chelation-assistance which could promote formation of cyclometallated complexes. The Lewis-basic directing group coordinates the Lewis-acidic metal bringing it in proximity to C-H bonds to be functionalized. The thermodynamic stability of cyclometallated complexes determines which C-H bonds are to be cleaved and functionalized. Relative thermodynamic stability favors formation of five-membered chelates, allowing the formation of mono five-membered-chelate (1, Figure 1) and double-five-membered chelates (2, Figure 1) by using monodentate and bidentate directing groups, respectively (Figure 1) [8]
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