Pd(II)-Catalyzed Direct Sulfonylation of Unactivated C(sp3)-H Bonds with Sodium Sulfinates

被引：107

作者：

Rao, Wei-Hao ^{[1
]}

Zhan, Bei-Bei ^{[1
]}

Chen, Kai ^{[1
]}

Ling, Peng-Xiang ^{[1
]}

Zhang, Zhuo-Zhuo ^{[1
]}

Shi, Bing-Feng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 14期

关键词：

C-S BOND; CATALYZED DIRECT THIOLATION; EFFICIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; C(SP(2))-H BONDS; TERMINAL ALKYNES; ARYL HALIDES; ARYLATION; FUNCTIONALIZATION; ALKYLATION;

D O I：

10.1021/acs.orglett.5b01634

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)-catalyzed sulfonylation of unactivated C(sp(3))-H bonds with sodium arylsulfinates using an 8-aminoquinoline auxiliary is described. This reaction demonstrates excellent functional group tolerance with respect to both the caboxamide starting material and the sodium arylsulfinate coupling partner, affording a broad range of aryl alkyl sulfones. Moreover, the late-stage modification of complex molecules was achieved via this sulfonylation protocol.

引用

页码：3552 / 3555

页数：4

共 64 条

[1]

[Anonymous], 2015, ACCOUNTS CHEM RES

[2] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[3] Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines [J].

Chan, Kelvin S. L. ;

Fu, Hai-Yan ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (05) :2042-2046

[4]

Chan KSL, 2014, NAT CHEM, V6, P146, DOI [10.1038/NCHEM.1836, 10.1038/nchem.1836]

[5] Palladium-triethylborane-triggered direct and regioselective conversion of allylic alcohols to allyl phenyl sulfones [J].

Chandrasekhar, S ;

Jagadeshwar, V ;

Saritha, B ;

Narsihmulu, C .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6506-6507

[6] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].

Chen, Fa-Jie ;

Zhao, Sheng ;

Hu, Fang ;

Chen, Kai ;

Zhang, Qi ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192

[7] Practical Synthesis of anti-β-Hydroxy-α-Amino Acids by PdII-Catalyzed Sequential C(sp3)-H Functionalization [J].

Chen, Kai ;

Zhang, Shuo-Qing ;

Jiang, Huai-Zhi ;

Xu, Jing-Wen ;

Shi, Bing-Feng .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (08) :3264-3270

[8] Sulfonamide-Promoted Palladium(II)-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Alkyl Iodides [J].

Chen, Kai ;

Shi, Bing-Feng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) :11950-11954

[9] A general and practical palladium-catalyzed monoarylation of β-methyl C(sp3)-H of alanine [J].

Chen, Kai ;

Zhang, Shuo-Qing ;

Xu, Jing-Wen ;

Hu, Fang ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2014, 50 (90) :13924-13927

[10] Pd(II)-catalyzed alkylation of unactivated C(sp3)-H bonds: efficient synthesis of optically active unnatural α-amino acids [J].

Chen, Kai ;

Hu, Fang ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL SCIENCE, 2013, 4 (10) :3906-3911

← 1 2 3 4 5 6 7 →