Recent Progress on Synthesis of N, N'-Chelate Organoboron Derivatives

Abstract

N,N'-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, biomedical research, or other practical science. Here, we summarized the organoboron-N,N'-chelate derivatives and showed the different routes of their syntheses. Traditional methods to synthesize N,N'-chelate organoboron compounds were mainly using bidentate ligand containing nitrogen reacting with trivalent boron reagents. In this review, we described a series of bidentate ligands, such as bipyridine, 2-(pyridin-2-yl)-1H-indole, 2-(5-methyl-1H-pyrrol-2-yl)quinoline, N-(quinolin-8-yl)acetamide, 1,10-phenanthroline, and diketopyrrolopyrrole (DPP).

Keywords: N,N′-chelate; fluorescent materials; organoboron; tetracoordinated.

Figure 1

Application of tetracoordinate organoboron complexes in luminescent materials, organic light-emitting diode (OLED), functional polymer, and photocatalyst [30,31,32,33,34,35,36].

Figure 2

The methods for the formation of N,N′-chelate organoboron derivatives [30,31,32,33,34,35,36].

Scheme 1

Reactions of bipyridine with dibutyl(((trifluoromethyl)sulfonyl)oxy)borane [37].

Scheme 2

Reactions of 2,5-di(pyridin-2-yl)pyrazine (or 2′, 2′: 4′, 4′: 2″, 2‴-quaterpyridine) with FcB(Me)Br [38].

Scheme 3

The methods for the synthesis of {Fc(Bbipy)₂O}(PF₆)₂ and {Fc(Bbipy)₂(OH)₂}(PF₆)₂ [39,40].

Scheme 4

Reactions of 4,4′-di(but-3-en-1-yl)-2,2′-bipyridine with trivalent boron [41].

Scheme 5

Reactions of bipyridine with 5-chloro-5,10-dihydrodibenzo[b,e]borinine [42].

Scheme 6

Bipyridine for the formation of N,N′-chelate organoboron and ferrocene derivatives [43].

Scheme 7

Bipyridine reacting with 5-bromo-10-mesityl-5,10-dihydroboranthrene [44].

Scheme 8

Reactions of 2-(pyridin-2-yl)-1H-indole and 2-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine with BPh₃ [36].

Scheme 9

Reactions of 2-(pyridin-2-yl)-1H-indole derivatives with BPh₃ [45].

Scheme 10

Reactions of 2-(1H-indol-2-yl)thiazole, 8-(1H-benzo[d]imidazol-2-yl)quinoline, and their analogues with BPh₃ [30].

Scheme 11

Reactions of 2-(pyridin-2-yl)-1H-indole with FcBMeBr [46].

Scheme 12

Reactions of 2-(1H-indol-7-yl)benzo[d]oxazole, 2-(1H-indol-7-yl)benzo[d]thiazole, and 2-(1H-indol-7-yl)-1-octyl-1H-benzo[d]imidazole with BPh₃ [32].

Scheme 13

Reactions of 2-(1H-pyrazol-5-yl)pyridine reacting with BPh₃ [47].

Scheme 14

Reactions of pyridin-2-ylmethanamine with hydroxydiphenylborane [48].

Scheme 15

Reactions of 2-(1H-pyrazol-5-yl)pyridine derivatives with BPh₃ [49].

Scheme 16

Reactions of 2-(4H-1,2,4-triazol-3-yl)pyridine derivatives with BPh₃ [50].

Scheme 17

Synthesis of 2-(3,5-bis(trifluoromethyl)-1H-pyrrol-2-yl)pyridine chelate organoboron complexes [33].

Scheme 18

Reactions of 2-(5-methyl-1H-pyrrol-2-yl)pyridine, 2-(pyridin-2-yl)-1H-indole, and (Z)-2-(phenyl(2H-pyrrol-2-ylidene)methyl)-1H-pyrrole with BPh₃ [51].

Scheme 19

Reactions of 2-(5-methyl-1H-pyrrol-2-yl)pyridine, 2-(5-methyl-1H-pyrrol-2-yl)quinoline, and 2-(5-methyl-1H-pyrrol-2-yl)quinoxaline with BPh₃ [52].

Scheme 20

Synthesis of BPh₂(2-(2-quinolyl)naphtho[b]imidazolato) and BPh₂(2-(2-quinolyl)benzimidazolato) [53].

Scheme 21

Synthesis of 1-(3-(trifluoromethyl)-1H-pyrazol-5-yl)isoquinoline chelate organoboron complexes [54].

Scheme 22

Reactions of N-(quinolin-8-yl)acetamide with BPh₃ [34].

Scheme 23

Synthesis of (S)-N-(1-((5-iodoquinolin-8-yl)amino)-1-oxopropan-2-yl)hexanamide chelate organoboron polymer [55].

Scheme 24

Synthesis of N-(5-iodoquinolin-8-yl)undecanamide chelate organoboron polymer [56].

Scheme 25

Synthesis of N-(quinolin-8-yl)acetamide chelate organoboron polymer [57].

Scheme 26

Synthesis of quinolin-8-amine chelate organoboron complex [58].

Scheme 27

Synthesis of 3-phenyl-N-(quinolin-8-yl)propanamide derivatives chelate organoboron photocatalysts [35].

Scheme 28

Synthesis of 2,2,2-trifluoro-N-(quinolin-8-yl)acetamide-based organoboron fluorescent complexes [31].

Scheme 29

Synthesis of 1,10-phenanthroline chelate organoboron complex [59].

Scheme 30

Synthesis of 1,10-phenanthroline chelate organoboron complex [60].

Scheme 31

Reactions of (9E,10E)-N⁹,N¹⁰-bis(6-methylheptyl)phenanthrene-9,10-diimine with trivalent boron [61].

Scheme 32

Synthesis of boron-coordinated diketopyrrolopyrrole (DPP) derivatives [62].

Scheme 33

Synthesis of boron-coordinated diketopyrrolopyrrole (DPP) derivatives [63].

Scheme 34

Reactions of 1,2,3,4,5-pentaphenyl-1H-borole with isocyanates [64].