A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions

被引：60

作者：

Greb, Andreas ^{[1
]}

Poh, Jian-Siang ^{[1
]}

Greed, Stephanie ^{[1
]}

Battilocchio, Claudio ^{[1
]}

Pasau, Patrick ^{[2
]}

Blakemore, David C. ^{[3
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[2] UCB Biopharma SPRL, Chem Res R5, Chemin Foriest, B-1420 Braine Lalleud, Belgium

[3] Pfizer Inc, Med Design, Eastern Point Rd, Groton, CT 06340 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

boronic acids; cross-coupling; diazo compounds; flow chemistry; photochemistry; TAMING HAZARDOUS CHEMISTRY; BORONIC ACIDS; FLOW; ARYLATION; TOOL;

D O I：

10.1002/anie.201710445

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon-carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp(2))-C(sp(3)) cross-coupling processes, with excellent functional-group tolerance.

引用

页码：16602 / 16605

页数：4

共 32 条

[1] THE SYNTHESIS AND SOME REACTIONS OF DIAZOCYCLOBUTANE [J].

APPLEQUIST, DE ;

MCGREER, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (08) :1965-1972

[2] Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine [J].

Bagutski, Viktor ;

Elford, Tim G. ;

Aggarwal, Varinder K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1080-1083

[3]

Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]

[4]

Battilocchio C, 2016, NAT CHEM, V8, P360, DOI [10.1038/NCHEM.2439, 10.1038/nchem.2439]

[5] Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids [J].

Bomio, Claudio ;

Kabeshov, Mikhail A. ;

Lit, Arthur R. ;

Lau, Shing-Hing ;

Ehlert, Janna ;

Battilocchio, Claudio ;

Ley, Steven V. .

CHEMICAL SCIENCE, 2017, 8 (09) :6071-6075

[6]

Bonet A, 2014, NAT CHEM, V6, P584, DOI [10.1038/nchem.1971, 10.1038/NCHEM.1971]

[7] Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 1.: 1-aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids [J].

Brackmann, Farina ;

de Meijere, Armin .

CHEMICAL REVIEWS, 2007, 107 (11) :4493-4537

[8]

CAMBIE C, 2016, CHEM REV, V116, P10276, DOI DOI 10.1039/C4SC03072A

[9] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

[10] Taming Hazardous Chemistry in Flow: The Continuous Processing of Diazo and Diazonium Compounds [J].

Deadman, Benjamin J. ;

Collins, Stuart G. ;

Maguire, Anita R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2298-2308

← 1 2 3 4 →