Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters

被引：19

作者：

Blackburn, J. Miles ^{[1
]}

Kanegusuku, Anastasia L. Gant ^{[1
]}

Scott, Georgia E. ^{[1
]}

Roizen, Jennifer L. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Box 90346, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

美国国家卫生研究院;

关键词：

SUZUKI-MIYAURA REACTIONS; CROSS-COUPLING REACTIONS; N BOND FORMATION; ARYL; AMINATION; PHOTOREDOX; ACID; ARYLATION; HALIDES; LIGAND;

D O I：

10.1021/acs.orglett.9b02621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.

引用

页码：7049 / 7054

页数：6

共 62 条

[1] Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Song, Weifeng .

ORGANIC LETTERS, 2011, 13 (07) :1784-1786

[2] Novel N-aryl and N-heteroaryl sulfamide synthesis via palladium cross coupling [J].

Alcaraz, L ;

Bennion, C ;

Morris, J ;

Meghani, P ;

Thom, SM .

ORGANIC LETTERS, 2004, 6 (16) :2705-2708

[3] Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes [J].

Ayer, Suraj K. ;

Roizen, J. L. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06) :3508-3523

[4] C-N bond forming cross-coupling reactions: an overview [J].

Bariwal, Jitender ;

Van der Eycken, Erik .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303

[5] Catalytic Strategies to Convert 2-Halopyridines to 2-Alkylpyridines [J].

Blackburn, J. Miles ;

Roizen, Jennifer L. .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (07) :920-930

[6] Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate [J].

Blackburn, J. Miles ;

Short, Melanie A. ;

Castanheiro, Thomas ;

Ayer, Suraj K. ;

Muellers, Tobias D. ;

Roizen, Jennifer L. .

ORGANIC LETTERS, 2017, 19 (21) :6012-6015

[7] New efficient nickey(0) catalysed amination of aryl chlorides [J].

Brenner, E ;

Fort, Y .

TETRAHEDRON LETTERS, 1998, 39 (30) :5359-5362

[8] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[9] The Liebeskind-Srogl Cross-Coupling Reaction and its Synthetic Applications [J].

Cheng, Hong-Gang ;

Chen, Han ;

Liu, Yue ;

Zhou, Qianghui .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (03) :490-508

[10] Advances in Base-Metal Catalysis: Development of a Screening Platform for Nickel-Catalyzed Borylations of Aryl (Pseudo)halides with B2(OH)4 [J].

Coombs, John R. ;

Green, Rebecca A. ;

Roberts, Frederick ;

Simmons, Eric M. ;

Stevens, Jason M. ;

Wisniewski, Steven R. .

ORGANOMETALLICS, 2019, 38 (01) :157-166

← 1 2 3 4 5 6 7 →