Palladium-catalyzed allylation of sulfonyl hydrazides with alkynes to synthesize allylic arylsulfones

被引：36

作者：

Lu, Chuan-Jun ^{[1
]}

Chen, Hong ^{[1
]}

Chen, Dong-Kai ^{[1
]}

Wang, Hong ^{[1
]}

Yang, Zhen-Ping ^{[1
]}

Gao, Jianrong ^{[1
]}

Jin, Hongwei ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Chaowang Rd 18, Hangzhou 310014, Zhejiang, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 46期

基金：

中国国家自然科学基金;

关键词：

INTRAMOLECULAR ASYMMETRIC HYDROAMINATION; REGIOSELECTIVE DECARBOXYLATIVE ADDITION; TERMINAL ALKYNES; BETA-KETOACIDS; ACID; SUBSTITUTION; SULFONYLHYDRAZIDES; PRONUCLEOPHILES; ALKYLATION; ALLENES;

D O I：

10.1039/c6ob01929c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the construction of allyl arylsulfone derivatives was developed by palladium catalyzed allylation of sulfonyl hydrazides with alkynes. A series of structurally diverse allyl arylsulfones can be regioselectively synthesized in high yields under mild conditions.

引用

页码：10833 / 10839

页数：7

共 61 条

[1] Sulfones: new reagents in organocatalysis [J].

Alba, Andrea-Nekane R. ;

Companyo, Xavier ;

Rios, Ramon .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033

[2] Intramolecular hydroamination of alkynes catalyzed by Pd(PPh3)4/triphenylphosphine under neutral conditions [J].

Bajracharya, GB ;

Huo, ZB ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4883-4886

[3] A NEW GENERAL-SYNTHESIS OF SULFONES FROM ALKYL OR ARYL HALIDES AND PARA-TOLUENESULFONHYDRAZIDE [J].

BALLINI, R ;

MARCANTONI, E ;

PETRINI, M .

TETRAHEDRON, 1989, 45 (21) :6791-6798

[4] Regioselective Rhodium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Terminal Alkynes [J].

Beck, Thorsten M. ;

Breit, Bernhard .

ORGANIC LETTERS, 2016, 18 (01) :124-127

[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] Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines [J].

Chen, Qing-An ;

Chen, Zhiwei ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8392-8395

[7] Sulfonyl Group-Containing Compounds in the Design of Potential Drugs for the Treatment of Diabetes and Its Complications [J].

Chen, X. ;

Hussain, S. ;

Parveen, S. ;

Zhang, S. ;

Yang, Y. ;

Zhu, C. .

CURRENT MEDICINAL CHEMISTRY, 2012, 19 (21) :3578-3604

[8] Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling [J].

Cruz, Faben A. ;

Chen, Zhiwei ;

Kurtoic, Sarah I. ;

Dong, Vy M. .

CHEMICAL COMMUNICATIONS, 2016, 52 (34) :5836-5839

[9] Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety [J].

El-Awa, Ahmad ;

Noshi, Mohammad N. ;

du Jourdin, Xavier Mollat ;

Fuchs, Philip L. .

CHEMICAL REVIEWS, 2009, 109 (06) :2315-2349

[10] Practical Pd/C-mediated allylic substitution in water [J].

Felpin, FX ;

Landais, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6441-6446

← 1 2 3 4 5 6 7 →