Experimental and Theoretical Study on Palladium-Catalyzed C-P Bond Formation via Direct Coupling of Triarylbismuths with P(O)-H Compounds

被引：71
作者：
Wang, Tao [1 ,2 ,3 ]
Sang, Shuai [1 ,2 ,3 ]
Liu, Liu [1 ,2 ,3 ,5 ]
Qiao, Hongwei [1 ,2 ,3 ]
Gao, Yuxing [1 ,2 ,3 ]
Zhao, Yufen [1 ,2 ,3 ,4 ]
机构：
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Xiamen Univ, Collaborat Innovat Ctr Chem Energy Mat iChEM, Xiamen 361005, Fujian, Peoples R China
[4] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[5] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 02期
关键词：
MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; POTENTIAL BASIS-SETS; POLARIZATION FUNCTIONS; H-PHOSPHONATES; ARYL HALIDES; ORGANOMETALLIC NUCLEOPHILES; ORGANOBISMUTH DIALKOXIDES; DIPHENYLPHOSPHINE OXIDE; OXIDATIVE ADDITION;
D O I：
10.1021/jo402392t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and highly efficient Pd-catalyzed cross-coupling of triarylbismuths with a variety of P(O)-H compounds has been developed that proceeds smoothly without exclusion of moisture or air and provides a general and powerful tool for the preparation of various valuable arylphosphonates, arylphosphinates, and arylphosphine oxides, with high atom-economy, operational simplicity of the procedure, and good to high yield. The coupling reaction is the first example of transition-metal-catalyzed C-P bond construction using triarylbismuth compounds as substrates. DFT calculations reveal that C-P bond formation is the rate-determing step.
引用
收藏
页码：608 / 617
页数：10
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