What is the difference between mono- and biphosphine ligands? Revealing the chemoselectivity in Pd-catalysed carbenation of bromonaphthalene

被引:1
作者
Gong, Wenting [1 ]
Fu, Dongmin [2 ,3 ]
Zhong, Kangbao [4 ,5 ]
Ni, Hao [4 ,5 ]
He, Xiaoqian [4 ,5 ]
Shan, Chunhui [1 ]
Li, Rong [1 ]
Lan, Yu [2 ,3 ,4 ,5 ]
机构
[1] Chongqing Normal Univ, Coll Chem, Chongqing Key Lab Inorgan Funct Mat, Chongqing 401331, Peoples R China
[2] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Henan, Peoples R China
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Henan, Peoples R China
[4] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
[5] Chongqing Univ, Chongqing Key Lab Theoret & Computat Chem, Chongqing 400030, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 18期
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
MIGRATORY INSERTION; HECK REACTION; MECHANISM; NICKEL; MONODENTATE; BROMOARENES; ACTIVATION; ORIGINS; ESTERS;
D O I
10.1039/d2qo00910b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ligand-controlled chemoselectivity is an important topic in organometallic chemistry. In this work, DFT calculations were used to reveal the chemoselectivity of a Pd-catalysed three-component dearomative carbenation of bromonaphthalene with diazo compounds and allylborates. When a monophosphine ligand was used, ligand exchange with a diazo compound was favored by the release of a phosphine ligand. Therefore, a three-component coupling reaction could occur. However, when a biphosphine ligand was used, ligand exchange between the phosphine and the diazo compounds was difficult. Therefore, the Suzuki-Miyaura coupling product was observed in this case, without the participation of the carbene moiety.
引用
收藏
页码:4916 / 4923
页数:8
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