BNN-1,3-dipoles: isolation and intramolecular cycloaddition with unactivated arenes

Guo, Rui1; Jiang, Jingxing2; Hu, Chenyang3,4; Liu, Liu Leo3,4; Cui, Ping1; Zhao, Meihua1; Ke, Zhuofeng2; Tung, Chen-Ho1; Kong, Lingbing1,5

2020-07-21

10.1039/d0sc02162h

Chemical Science   影响因子和分区

2041-6520

2041-6539

The mono-base-stabilized 1,2-diboranylidenehydrazine derivatives featuring a 1,3-dipolar BNN skeleton are obtained by dehydrobromination of [ArB(Br)NH](2)(Ar = 2,6-diphenylphenyl (Dpp), Ar = 2,6-bis(2,4,6-trimethylphenyl)phenyl (Dmp) or Ar = 2,4,6-tri-tert-butylphenyl (Mes*)) with N-heterocyclic carbenes (NHCs). Depending on the Ar substituents, such species can be isolated as a crystalline solid (Ar = Mes*) or generated as reactive intermediates undergoing spontaneous intramolecular aminoboration of the proximal arene ringsvia[3 + 2] cycloaddition (Ar = Dpp or Dmp). The latter reactions showcase the 1,3-dipolar reactivity toward unactivated arenes at ambient temperature. In addition, double cycloaddition of the isolable BNN species with two CO(2)molecules affords a bicyclic species consisting of two fused five-membered BN2CO rings. The electronic structures of these BNN species and the mechanisms of these cascade reactions are interrogated through density functional theory (DFT) calculations.

SCI ; IC ; EI

英语

NI论文

其他

Natural Science Foundation of China[21971144][21702228][21673301] ; Natural Science Foundation of Shandong Province[ZR2019ZD46][ZR2017MB021] ; Key R&D Program of Shandong Province[2019GGX102032] ; Guangdong Natural Science Funds for Distinguished Young Scholars[2015A030306027] ; Qilu Youth Scholar Funding of Shandong University[11190088963021] ; Multidisciplinary Research and Innovation Team of Young Scholars of Shandong University[2020QNQT007]

Chemistry

Chemistry, Multidisciplinary

WOS:000548733200009

ROYAL SOC CHEMISTRY

20203008963789

Electronic structure ; Aromatic compounds

Organic Compounds:804.1 ; Probability Theory:922.1 ; Atomic and Molecular Physics:931.3 ; Quantum Theory; Quantum Mechanics:931.4

Web of Science

1.Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Minist Educ, Jinan 250100, Peoples R China
2.Sun Yat Sen Univ, Sch Mat Sci & Engn, PCFM Lab, Guangzhou 510275, Guangdong, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
5.Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

Guo, Rui,Jiang, Jingxing,Hu, Chenyang,et al. BNN-1,3-dipoles: isolation and intramolecular cycloaddition with unactivated arenes[J]. Chemical Science,2020,11(27):7053-7059.

Guo, Rui.,Jiang, Jingxing.,Hu, Chenyang.,Liu, Liu Leo.,Cui, Ping.,...&Kong, Lingbing.(2020).BNN-1,3-dipoles: isolation and intramolecular cycloaddition with unactivated arenes.Chemical Science,11(27),7053-7059.

Guo, Rui,et al."BNN-1,3-dipoles: isolation and intramolecular cycloaddition with unactivated arenes".Chemical Science 11.27(2020):7053-7059.