Room temperature Ni-catalyzed reduction of aryl tosylates by borane hydrides

被引：14

作者：

Kogan, Vladimir ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Koffolk Fine Chem Ltd, IL-84874 Ramat Hovav, Israel

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 43期

关键词：

D O I：

10.1016/j.tetlet.2006.08.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild Ni-catalyzed homogeneous reductions of aryl tosylates are described for the first time. The catalytic system Ni(PPh3)(2)Cl-2 and PCy3 is shown to be general for hydrogenolysis of a wide range of tosylates, including hindered, deactivated, heterocyclic, and bifunctional examples. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：7515 / 7518

页数：4

共 29 条

[1] PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES [J].

BADONE, D ;

CECCHI, R ;

GUZZI, U .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6321-6323

[2]

Bolm C, 2000, SYNTHESIS-STUTTGART, P911

[3] PALLADIUM-CATALYZED REDUCTION OF ARYL SULFONATES - REDUCTION VERSUS HYDROLYSIS AND SELECTIVITY CONTROL [J].

CABRI, W ;

DEBERNARDINIS, S ;

FRANCALANCI, F ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :350-353

[4] PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (45) :5541-5544

[5] Application of the Suzuki reaction as the key step in the synthesis of a novel atropisomeric biphenyl derivative for use as a liquid crystal dopant [J].

Cammidge, AN ;

Crépy, KVL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6832-6835

[6] Synthesis of calix[4]arene triflates and their unusual chemical reactivity in palladium-catalyzed reactions [J].

Chowdhury, S ;

Bridson, JN ;

Georghiou, PE .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3299-3302

[7]

DRISSA S, 2004, SYNLETT, P2612

[8]

Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2700, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO

[9]

2-P

[10] First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction [J].

Fu, XY ;

Zhang, SY ;

Yin, JG ;

McAllister, TL ;

Jiang, SA ;

Tann, CH ;

Thiruvengadam, TK ;

Zhang, FC .

TETRAHEDRON LETTERS, 2002, 43 (04) :573-576

← 1 2 3 →