A Synthesis of "Dual Warhead" β-Aryl Ethenesulfonyl Fluorides and One-Pot Reaction to β-Sultams

被引：85

作者：

Chinthakindi, Praveen K. ^{[1
]}

Govender, Kirnberleigh B. ^{[1
]}

Kurnar, A. Sanjeeva ^{[1
]}

Kruger, Hendrik G. ^{[1
]}

Govender, Thavendran ^{[1
]}

Naicker, Tricia ^{[1
]}

Arvidsson, Per I. ^{[1
,2
,3
]}

机构：

[1] Univ KwaZulu Natal, Catalysis & Peptide Res Unit, Durban, South Africa

[2] Karolinska Inst, Sci Life Lab, Drug Discovery & Dev Platform, Dept Med Biochem & Biophys, Stockholm, Sweden

[3] Karolinska Inst, Dept Med Biochem & Biophys, Div Translat Med & Chem Biol, Stockholm, Sweden

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 03期

基金：

新加坡国家研究基金会;

关键词：

ARYLBORONIC ACIDS; SULFONYL FLUORIDES; OXIDATIVE HECK; CONJUGATE ADDITION; CATALYZED PROTODEBORONATION; CHEMICAL BIOLOGY; CLICK CHEMISTRY; SUFEX CLICK; SULFONIMIDAMIDES; ELECTROPHILES;

D O I：

10.1021/acs.orglett.6b03634

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an operationally simple, ligand- and additive-free oxidative boron-Heck coupling that is compatible with the ethenesulfonyl fluoride functional group. The protocol proceeds at room temperature with chemo-selectivity and E-isomer selectivity and offers facile access to a wide range of beta-aryl/heteroaryl ethenesulfonyl fluorides from commercial boronic acids. Furthermore, we demonstrate a one-pot click" reaction to directly transform the products to aryl-substituted beta-sultams.

引用

页码：480 / 483

页数：4

共 40 条

[1] Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry [J].

Andappan, Murugaiah M. S. ;

Nilsson, Peter ;

Larhed, Mats .

MOLECULAR DIVERSITY, 2003, 7 (2-4) :97-106

[2] Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides [J].

Bogolubsky, Andrey V. ;

Moroz, Yurii S. ;

Mykhailiuk, Pavel K. ;

Pipko, Sergey E. ;

Konovets, Anzhelika I. ;

Sadkova, Irina V. ;

Tolmachev, Andrey .

ACS COMBINATORIAL SCIENCE, 2014, 16 (04) :192-197

[3] Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous Precursor [J].

Borhade, Sanjay R. ;

Sandstrom, Anja ;

Arvidsson, Per I. .

ORGANIC LETTERS, 2013, 15 (05) :1056-1059

[4] Proteasome inhibition by new dual warhead containing peptido vinyl sulfonyl fluorides [J].

Brouwer, Arwin J. ;

Alvarez, Natalia Herrero ;

Ciaffoni, Adriano ;

van de Langemheen, Helmus ;

Liskamp, Rob M. J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (16) :3429-3435

[5] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].

Cernak, Tim ;

Dykstra, Kevin D. ;

Tyagarajan, Sriram ;

Vachal, Petr ;

Krska, Shane W. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576

[6] Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found? [J].

Chen, Quan ;

Mayer, Peter ;

Mayr, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (41) :12664-12667

[7] On-Water Synthesis of Biaryl Sulfonyl Fluorides [J].

Chinthakindi, Praveen K. ;

Kruger, Hendrik G. ;

Govender, Thavendran ;

Naicker, Tricia ;

Arvidsson, Per I. .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2618-2623

[8] Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps [J].

Dickstein, Joshua S. ;

Curto, John M. ;

Gutierrez, Osvaldo ;

Mulrooney, Carol A. ;

Kozlowski, Marisa C. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) :4744-4761

[9] Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry [J].

Dong, Jiajia ;

Krasnova, Larissa ;

Finn, M. G. ;

Sharpless, K. Barry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9430-9448

[10] Mizoroki-heck type reaction of organoboron reagents with alkenes and alkynes.: A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant [J].

Du, XL ;

Suguro, M ;

Hirabayashi, K ;

Mori, A ;

Nishikata, T ;

Hagiwara, N ;

Kawata, K ;

Okeda, T ;

Wang, HF ;

Fugami, K ;

Kosugi, M .

ORGANIC LETTERS, 2001, 3 (21) :3313-3316

← 1 2 3 4 →