Theoretical Investigation of the Mechanism of Rh(III)-catalyzed Annulation of 2-Biphenylboronic Acid with Activated Alkene

doi:10.1007/s40242-022-2187-6

Chemical Research in Chinese Universities ›› 2023, Vol. 39 ›› Issue (2): 276-282.doi: 10.1007/s40242-022-2187-6

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Theoretical Investigation of the Mechanism of Rh(III)-catalyzed Annulation of 2-Biphenylboronic Acid with Activated Alkene

LU Nan, MIAO Chengxia, LAN Xiaozheng

College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018, P. R. China

Received:2022-06-04 Online:2023-04-01 Published:2023-03-16
Contact: LU Nan E-mail:lun@sdau.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (Nos.21973056, 21972079), the Natural Science Foundation of Shandong Province, China(No.ZR2019MB050) and the Project of the Key Laboratory of Agricultural Film Application of Ministry of Agriculture and Rural Affairs, China.

Abstract

Abstract: The mechanism is investigated for Cp^tBuRh(OH)₂-catalyzed annulation of 2-biphenylboronic acid with three activated alkenes using M06-2X functional. The reaction comprises transmetalation via two steps and following C-H activation producing reactive Rh-biphenyl complex with two Rh—C σ bonds. After the coordination/insertion of alkenes, respective fused or bridged cyclic products are yielded depending on different alkenes accompanied by the release of Cp^tBuRh. The promotion of Cp^tBuRh(OH)₂ lies in the barrier decrease of transmetalation and C-H activation ready for coordination/insertion ensuring the smooth progress of common rate-limiting reductive elimination. The stereoselective transfer and ring rotation are specific for benzoquinone and cyclopropenone. The role of Rh(III) catalyst and release of Rh(I) is supported by Multiwfn analysis on frontier molecular orbital(FMO) of specific transiton states(TSs) and Mayer bond order(MBO) value of vital bonding, breaking.

Key words: Annulation, Activated alkene, Transmetalation, Coordination/insertion, M06-2X functional

LU Nan, MIAO Chengxia, LAN Xiaozheng. Theoretical Investigation of the Mechanism of Rh(III)-catalyzed Annulation of 2-Biphenylboronic Acid with Activated Alkene[J]. Chemical Research in Chinese Universities, 2023, 39(2): 276-282.

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Theoretical Investigation of the Mechanism of Rh(III)-catalyzed Annulation of 2-Biphenylboronic Acid with Activated Alkene

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