Aromatic 1,4,2,3-Diazadiborole Featuring an Unsymmetrical B=B Entity: A Versatile Synthon for Unusual Boron Heterocycles

Mu, Yu1; Dai, Yuyang1; Ruiz, David A.2,3; Liu, Liu Leo2,3; Xu, Li-Ping1; Tung, Chen-Ho1; Kong, Lingbing1,4

2024-07-01

10.1002/anie.202405905

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

["The replacement of a CC unit with an isoelectronic BN unit in aromatic systems can give rise to molecules and materials with fascinating properties. We report here the synthesis, characterization, and reactivity of a 1,4,2,3-diazadiborole species, 2, featuring an unprecedented 6 pi-aromatic BN-heterocyclic moiety that is isoelectronic to cyclopentadienide (Cp-). Bearing an unsymmetrical B=B entity, 2 exhibits reactivity toward oxidants, protic reagents, electrophiles, and unsaturated substrates. This reactivity facilitates the synthesis of a variety of novel mono- and bicyclic organoboron derivatives through mechanisms including ring retention, cleavage/recombination, annulation, and expansion. These findings reveal innovative synthetic routes to BN-embedded aromatic compounds via desymmetrization, affording unique building blocks for synthetic chemistry.","This work unveils a 6 pi-aromatic 1,4,2,3-diazadiborole, a BN analogue of cyclopentadienide. Featuring an unsymmetrical B=B entity, this species readily undergoes redox, insertion, addition, and cycloaddition reactions for the synthesis of unusual boron heterocycles. The ring retention, cleavage/recombination, annulation, and expansion have been witnessed during these transformations. image"]

BN-embedded aromatics Unsymmetrical diborenes Redox property Insertion Cycloaddition

SCI ; EI

英语

其他

National Natural Science Foundation of China[22271174] ; Taishan Scholar Project of Shandong Province of China[tsqn202211007] ; Natural Science Foundation of Shandong Province[ZR2019ZD46] ; Multidisciplinary Research and Innovation Team of Young Scholars of Shandong University[2020QNQT007]

Chemistry

Chemistry, Multidisciplinary

WOS:001261697500001

WILEY-V C H VERLAG GMBH

20242716654249

Aromatic compounds ; Aromatization ; Boron ; Steel beams and girders

Structural Members and Shapes:408.2 ; Steel:545.3 ; Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

Web of Science

1.Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Res Ctr Chem Biol & Om Anal, Coll Sci, Shenzhen 518055, Peoples R China
4.Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China

Mu, Yu,Dai, Yuyang,Ruiz, David A.,et al. Aromatic 1,4,2,3-Diazadiborole Featuring an Unsymmetrical B=B Entity: A Versatile Synthon for Unusual Boron Heterocycles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024,63.

Mu, Yu.,Dai, Yuyang.,Ruiz, David A..,Liu, Liu Leo.,Xu, Li-Ping.,...&Kong, Lingbing.(2024).Aromatic 1,4,2,3-Diazadiborole Featuring an Unsymmetrical B=B Entity: A Versatile Synthon for Unusual Boron Heterocycles.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,63.

Mu, Yu,et al."Aromatic 1,4,2,3-Diazadiborole Featuring an Unsymmetrical B=B Entity: A Versatile Synthon for Unusual Boron Heterocycles".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63(2024).