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

页码：1108 / 1112

页数：5

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