Microwave-Mediated Suzuki-Miyaura Cross-Couplings of Thioether- and ortho-Substituted Methylphenylboronic Acid Esters

被引：4

作者：

Baltus, Christine B. ^{[1
]}

Press, Neil J. ^{[2
]}

Spencer, John ^{[1
]}

机构：

[1] Univ Greenwich, Univ Greenwich Medway, Sch Sci, Chatham ME4 4TB, Kent, England

[2] Novartis Pharmaceut UK Ltd, Horsham RH12 5AB, Sussex, England

来源：

SYNLETT | 2012年 / 17期

关键词：

palladium; catalysis; cross-coupling; biaryls; micro-waves;

D O I：

10.1055/s-0032-1317205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hiterto unsuccessful cross-couplings of ortho-substituted or thioether-substituted methylphenylboronates have now been achieved, under microwave conditions, enabling the synthesis of a library of novel biaryls. Tetrakis(triphenylphosphine) palladium and various bases, for example, sodium carbonate or cesium fluoride, were found to mediate the crucial C-C bond-forming cross-coupling reaction.

引用

页码：2477 / 2480

页数：4

共 9 条

[1]

Baltus C. B., 2011, THESIS U GREENWICH U

[2] Practical thiol surrogates and protective groups for arylthiols for Suzuki-Miyaura conditions [J].

Itoh, T ;

Mase, T .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2203-2206

[3] Cyclopalladation of meta-(Diphenylthiophosphoryloxy)benzaldimines: NCS and Unexpected NCO 5,6-Membered Pincer Palladium Complexes [J].

Kozlov, V. A. ;

Aleksanyan, D. V. ;

Nelyubina, Yu. V. ;

Lyssenko, K. A. ;

Vasil'ev, A. A. ;

Petrovskii, P. V. ;

Odinets, I. L. .

ORGANOMETALLICS, 2010, 29 (09) :2054-2062

[4] Rapid and amenable Suzuki coupling reaction in water using microwave and conventional heating [J].

Leadbeater, NE ;

Marco, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :888-892

[5]

Morales-Morales D., 2007, CHEM PINCER COMPOUND

[6] Synthesis of ortho-modified mercapto- and piperazino-methyl-phenylboronic acid derivatives [J].

Spencer, J ;

Burd, AP ;

Goodwin, CA ;

Mérette, SAM ;

Scully, MF ;

Adatia, T ;

Deadman, JJ .

TETRAHEDRON, 2002, 58 (08) :1551-1556

[7]

SPENCER J, UNPUB

[8] Synthesis of a (piperazin-1-ylmethyl)biaryl library via microwave-mediated Suzuki-Miyaura cross-couplings [J].

Spencer, John ;

Baltus, Christine B. ;

Press, Neil J. ;

Harrington, Ross W. ;

Clegg, William .

TETRAHEDRON LETTERS, 2011, 52 (31) :3963-3968

[9] Microwave-Mediated Synthesis of an Arylboronate Library [J].

Spencer, John ;

Baltus, Christine B. ;

Patel, Hiren ;

Press, Neil J. ;

Callear, Samantha K. ;

Male, Louise ;

Coles, Simon J. .

ACS COMBINATORIAL SCIENCE, 2011, 13 (01) :24-31

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