Unveiling Hetero-Enyne Reactivity of Aryliminoboranes: Dearomative Hetero-Diels-Alder-Like Reactions

Qiu，Shuang1; Zhang，Xin2; Hu，Chaopeng2; Chu，Hongxu1; Li，Qianli3; Ruiz，David A.2; Liu，Liu Leo2; Tung，Chen Ho1; Kong，Lingbing1,4

2022-07-01

10.1002/anie.202205814

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Being isoelectronic with alkynes, iminoboranes with a polar B N triple bond have been exclusively investigated as a potent 1,2-dipole in synthetic chemistry. Herein, we disclose the unprecedented reactivity of aryliminoboranes via the BNCC pi conjugation, namely hetero-enyne behavior. This allows for facile dearomative Diels-Alder-like reactions of aryliminoboranes with aldehydes. This cycloaddition features mild conditions, is catalyst-free, and has a broad substrate scope and good functional group tolerance. Kinetic and computational studies reveal its second-order reaction and concerted cyclization mechanism. This report unveils new synthetic application of iminoboranes beyond their classical reaction patterns.

Aldehydes Aryliminoboranes Fused Heterocycles Hetero-Diels-Alder Reaction pi-Conjugation

SCI ; EI

英语

NI论文

通讯

NSFC["21971144","21702228","22101114"] ; Key R&D Program of Shandong (SD) Province[2019GGX102032] ; NSF of SD Province[ZR2019ZD46] ; Qilu Youth Scholar Funding of SDU[11190088963021] ; Multidisciplinary Research and Innovation Team of Young Scholars of SDU[2020QNQT007] ; Fundamental Research Funds for the Central Universities[2021JCG019] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000824619100001

WILEY-V C H VERLAG GMBH

20222912365289

Cyclization ; Cycloaddition

Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

2-s2.0-85133953982

Web of Science

1.School of Chemistry and Chemical Engineering,Shandong University,Jinan,250100,China
2.Department of Chemistry,Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
3.School of Chemistry and Chemical Engineering,Liaocheng University,Liaocheng,252059,China
4.State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin,300071,China

Qiu，Shuang,Zhang，Xin,Hu，Chaopeng,et al. Unveiling Hetero-Enyne Reactivity of Aryliminoboranes: Dearomative Hetero-Diels-Alder-Like Reactions[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022.

Qiu，Shuang.,Zhang，Xin.,Hu，Chaopeng.,Chu，Hongxu.,Li，Qianli.,...&Kong，Lingbing.(2022).Unveiling Hetero-Enyne Reactivity of Aryliminoboranes: Dearomative Hetero-Diels-Alder-Like Reactions.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.

Qiu，Shuang,et al."Unveiling Hetero-Enyne Reactivity of Aryliminoboranes: Dearomative Hetero-Diels-Alder-Like Reactions".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022).