Visible Light-Promoted Formation of C-B and C-S Bonds under Metal- and Photocatalyst-Free Conditions

被引：50

作者：

Blank, Lena ^{[1
]}

Fagnoni, Maurizio ^{[2
]}

Protti, Stefano ^{[2
]}

Ruepin, Magnus ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 05期

关键词：

arylazo sulfones; aryl radicals; arylboronic esters; aryl sulfides; CROSS-COUPLING REACTION; PALLADIUM-CATALYZED BORYLATION; ARYL HALIDES; PHARMACOLOGICAL-PROPERTIES; STEREOSELECTIVE-SYNTHESIS; PHOTOINDUCED BORYLATION; ARYLDIAZONIUM SALTS; SELECTIVE REACTIONS; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE;

D O I：

10.1055/s-0037-1611648

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- and additive-free carbon-heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.

引用

页码：1243 / 1252

页数：10

共 98 条

[1] Synthesis and reactivity of cobalt boryl complexes [J].

Adams, CJ ;

Baber, RA ;

Batsanov, AS ;

Bramham, G ;

Charmant, JPH ;

Haddow, MF ;

Howard, JAK ;

Lam, WH ;

Lin, ZY ;

Marder, TB ;

Norman, NC ;

Orpen, AG .

DALTON TRANSACTIONS, 2006, (11) :1370-1373

[2] Anti-infectives - Recent progress on the topical therapy of onychomycosis [J].

Alley, Michael R. K. ;

Baker, Stephen J. ;

Beutner, Karl R. ;

Plattner, Jacob .

EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2007, 16 (02) :157-167

[3] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid [J].

Antilla, JC ;

Wulff, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5099-5100

[4] Boron-Based Drug Design [J].

Ban, Hyun Seung ;

Nakamura, Hiroyuki .

CHEMICAL RECORD, 2015, 15 (03) :616-635

[5] Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents [J].

Baron, O ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3133-3135

[6] SNAr Reactions of Nitro-(pentafluorosulfanyl)benzenes To Generate SF5 Aryl Ethers and Sulfides [J].

Beier, Petr ;

Pastyrikova, Tereza ;

Vida, Norbert ;

Iakobson, George .

ORGANIC LETTERS, 2011, 13 (06) :1466-1469

[7]

Benquing C, 2017, CHEM COMMUN, V53, P12738

[8] Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons [J].

Bhanuchandra, M. ;

Baralle, Alexandre ;

Otsuka, Shinya ;

Nogi, Keisuke ;

Yorimitsu, Hideki ;

Osuka, Atsuhiro .

ORGANIC LETTERS, 2016, 18 (12) :2966-2969

[9] Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].

Billingsley, Kelvin L. ;

Barder, Timothy E. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363

[10] Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature [J].

Bose, Shubhankar Kumar ;

Marder, Todd B. .

ORGANIC LETTERS, 2014, 16 (17) :4562-4565

← 1 2 3 4 5 6 7 8 9 10 →