Spectroscopic and Structural Characterization of the CyNHC Adduct of B2pin2 in Solution and in the Solid State

被引：105

作者：

Kleeberg, Christian ^{[1
]}

Crawford, Andrew G. ^{[1
]}

Batsanov, Andrei S. ^{[1
]}

Hodgkinson, Paul ^{[1
]}

Apperley, David C. ^{[1
]}

Cheung, Man Sing ^{[2
]}

Lin, Zhenyang ^{[2
]}

Marder, Todd B. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; BORON CONJUGATE ADDITIONS; ASYMMETRIC BETA-BORATION; N-HETEROCYCLIC CARBENE; LEWIS-BASE ADDUCTS; DIBORON COMPOUNDS; REACTIVITY; COMPLEXES; BIS(PINACOLATO)DIBORON; ACTIVATION;

D O I：

10.1021/jo202127c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis base adduct of B(2)pin(2) and the NHC (1,3-bis(cydohexyl)imidazol-2-ylidene), which was proposed to act as a source of nucleophilic boryl groups in the beta-borylation of alpha,beta-unsaturated ketones, has been isolated, and its solid state structure and solution behavior was studied. In solution, the binding is weak, and NMR spectroscopy reveals a rapid exchange of the NHC between the two boron centers. DFT calculations reveal that the exchange involves dissociation and reassociation of NHC rather than an intramolecular process.

引用

页码：785 / 789

页数：5

共 50 条

[1] NHC's in catalyzed borylation chemistry: Their role as ligands on copper and in adduct formation with B2pin2
Marder, Todd B.
Kleeberg, Christian
Lin, Zhenyang
Liu, Lei
Steel, Patrick G.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[2] Selective Electroreductive Hydroboration of Olefins with B2pin2
Guo, Chengcheng
Li, Pengfei
Wang, Siyi
Wang, Yanwei
Liu, Ning
Bu, Qingqing
Qiu, Youai
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07): : 4569 - 4580
[3] Pd-Catalyzed Hydroboration of Vinylarenes with B2pin2
Wan, Yunhui
Lu, Yingpeng
Ren, Yi
Xu, Hongxi
Zhao, Gang
Zheng, Changwu
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9056 - 9062
[4] Reductive Aromatization of Quinols with B2pin2 as Deoxidizing Agent
Liu, Bin
Xu, Yin
Luo, Zhibin
Xie, Jimin
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (07) : 1022 - 1024
[5] Copper-catalyzed borofunctionalization of styrenes with B2pin2 and CO
Yuan, Yang
Wu, Fu-Peng
Wu, Xiao-Feng
CHEMICAL SCIENCE, 2021, 12 (41) : 13777 - 13781
[6] Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
Wang, Rongkang
Chen, Fangming
Jiang, Lvqi
Yi, Wenbin
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) : 1904 - 1911
[7] Palladium on carbon as an efficient, durable and economical catalyst for the alcoholysis of B2pin2
Zhou, Junjie
Li, Ning
Shen, Jialu
Meng, Xu
Liu, Xiang
INORGANIC CHEMISTRY COMMUNICATIONS, 2021, 130
[8] Synthesis of anti-vicinal diboronates from diarylethynes and B2pin2
Kuang, Zhijie
Mai, Shaoyu
Yang, Kai
Song, Qiuling
SCIENCE BULLETIN, 2019, 64 (22) : 1685 - 1690
[9] Synthesis of anti-vicinal diboronates from diarylethynes and B2pin2
Zhijie Kuang
Shaoyu Mai
Kai Yang
Qiuling Song
Science Bulletin, 2019, 64 (22) : 1685 - 1690
[10] Palladium-catalyzed regioselective hydroboration of aryl alkenes with B2pin2
Huang, Jiuzhong
Yan, Wuxin
Tan, Chaowei
Wu, Wanqing
Jiang, Huanfeng
CHEMICAL COMMUNICATIONS, 2018, 54 (14) : 1770 - 1773

← 1 2 3 4 5 →