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Review
. 2021 Mar 5;26(5):1401.
doi: 10.3390/molecules26051401.

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

Tianbao Yang  1 , Niu Tang  1 , Qizhong Wan  1 , Shuang-Feng Yin  1 , Renhua Qiu  1
Affiliations
Review

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

Tianbao Yang et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
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
Figure 2
The methods for the formation of N,N′-chelate organoboron derivatives [30,31,32,33,34,35,36].
Scheme 1
Scheme 1
Reactions of bipyridine with dibutyl(((trifluoromethyl)sulfonyl)oxy)borane [37].
Scheme 2
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
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
Scheme 4
Reactions of 4,4′-di(but-3-en-1-yl)-2,2′-bipyridine with trivalent boron [41].
Scheme 5
Scheme 5
Reactions of bipyridine with 5-chloro-5,10-dihydrodibenzo[b,e]borinine [42].
Scheme 6
Scheme 6
Bipyridine for the formation of N,N′-chelate organoboron and ferrocene derivatives [43].
Scheme 7
Scheme 7
Bipyridine reacting with 5-bromo-10-mesityl-5,10-dihydroboranthrene [44].
Scheme 8
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
Scheme 9
Reactions of 2-(pyridin-2-yl)-1H-indole derivatives with BPh3 [45].
Scheme 10
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
Scheme 11
Reactions of 2-(pyridin-2-yl)-1H-indole with FcBMeBr [46].
Scheme 12
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
Scheme 13
Reactions of 2-(1H-pyrazol-5-yl)pyridine reacting with BPh3 [47].
Scheme 14
Scheme 14
Reactions of pyridin-2-ylmethanamine with hydroxydiphenylborane [48].
Scheme 15
Scheme 15
Reactions of 2-(1H-pyrazol-5-yl)pyridine derivatives with BPh3 [49].
Scheme 16
Scheme 16
Reactions of 2-(4H-1,2,4-triazol-3-yl)pyridine derivatives with BPh3 [50].
Scheme 17
Scheme 17
Synthesis of 2-(3,5-bis(trifluoromethyl)-1H-pyrrol-2-yl)pyridine chelate organoboron complexes [33].
Scheme 18
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
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
Scheme 20
Synthesis of BPh2(2-(2-quinolyl)naphtho[b]imidazolato) and BPh2(2-(2-quinolyl)benzimidazolato) [53].
Scheme 21
Scheme 21
Synthesis of 1-(3-(trifluoromethyl)-1H-pyrazol-5-yl)isoquinoline chelate organoboron complexes [54].
Scheme 22
Scheme 22
Reactions of N-(quinolin-8-yl)acetamide with BPh3 [34].
Scheme 23
Scheme 23
Synthesis of (S)-N-(1-((5-iodoquinolin-8-yl)amino)-1-oxopropan-2-yl)hexanamide chelate organoboron polymer [55].
Scheme 24
Scheme 24
Synthesis of N-(5-iodoquinolin-8-yl)undecanamide chelate organoboron polymer [56].
Scheme 25
Scheme 25
Synthesis of N-(quinolin-8-yl)acetamide chelate organoboron polymer [57].
Scheme 26
Scheme 26
Synthesis of quinolin-8-amine chelate organoboron complex [58].
Scheme 27
Scheme 27
Synthesis of 3-phenyl-N-(quinolin-8-yl)propanamide derivatives chelate organoboron photocatalysts [35].
Scheme 28
Scheme 28
Synthesis of 2,2,2-trifluoro-N-(quinolin-8-yl)acetamide-based organoboron fluorescent complexes [31].
Scheme 29
Scheme 29
Synthesis of 1,10-phenanthroline chelate organoboron complex [59].
Scheme 30
Scheme 30
Synthesis of 1,10-phenanthroline chelate organoboron complex [60].
Scheme 31
Scheme 31
Reactions of (9E,10E)-N9,N10-bis(6-methylheptyl)phenanthrene-9,10-diimine with trivalent boron [61].
Scheme 32
Scheme 32
Synthesis of boron-coordinated diketopyrrolopyrrole (DPP) derivatives [62].
Scheme 33
Scheme 33
Synthesis of boron-coordinated diketopyrrolopyrrole (DPP) derivatives [63].
Scheme 34
Scheme 34
Reactions of 1,2,3,4,5-pentaphenyl-1H-borole with isocyanates [64].
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