Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions

被引：78
|
作者：
Nambo, Masakazu [1 ]
Keske, Eric C. [2 ]
Rygus, Jason P. G. [2 ]
Yim, Jacky C. -H. [1 ]
Crudden, Cathleen M. [1 ]
机构：
[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi, Japan
[2] Queens Univ, Dept Chem, Chernoff Hall, Kingston, ON, Canada
来源：
ACS CATALYSIS | 2017年 / 7卷 / 02期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
sulfone; Suzuki-Miyaura cross-coupling; C-SO2; activation; palladium catalysis; iterative coupling; PROTECTING GROUP-FREE; DIRECTING GROUPS; PHENYL SULFONE; ARYL BROMIDES; CATALYSIS; TRIARYLMETHANES; HETEROARENES; ACTIVATION; ARYLATION; REAGENTS;
D O I：
10.1021/acscatal.6b03434
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of C-SO2 bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked versus common electrophiles and its use in iterative cross-couplings for concise synthesis of biologically active molecules is described.
引用
收藏
页码：1108 / 1112
页数：5
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