Definitive evidence for the insertion of terminal alkynes into ArylS-Pt bonds:: "o-halogen effect" in stoichiometric and catalytic reactions

被引：44

作者：

Kuniyasu, Hitoshi ^{[1
]}

Yamashita, Fumikazu ^{[1
]}

Terao, Jun ^{[1
]}

Kambe, Nobuaki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 31期

关键词：

alkynes; insertion; neighboring-group effects; platinum; S ligands;

D O I：

10.1002/anie.200604986

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) An unexpected acceleration of the insertion of terminal alkynes into the S-Pt bond of complexes 1 was observed when an o-halogen substituent was present in the SAr moiety (see scheme). The reaction rates for G = o-Cl, o-Br, or o-l were much greater than for electron-donating or electron-withdrawing groups. This o-halogen effect" was also found to be relevant to the Pd-catalyzed addition of (ArS)2 to alkynes. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：5929 / 5933

页数：5

共 53 条

[11] Molecular orbital study of the mechanism of platinum(0)-catalyzed alkene and alkyne diboration reactions [J].

Cui, Q ;

Musaev, DG ;

Morokuma, K .

ORGANOMETALLICS, 1997, 16 (07) :1355-1364

[12] METAL PERFLUORO-ALKANE-AND-ARENE-THIOLATES .4. REACTIONS OF SOME MANGANESE, IRON, AND COBALT DERIVATIVES WITH ALKYNES [J].

DAVIDSON, JL ;

SHARP, DWA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1975, (21) :2283-2287

[13] Directed reactivity at a vanadium(II) thiolate center: synthesis and structure of a novel vanadium thiolate complex and its reaction product with azobenzene [J].

Davis, JA ;

Davie, CP ;

Sable, DB ;

Armstrong, WH .

CHEMICAL COMMUNICATIONS, 1998, (16) :1649-1650

[14]

Gareau Y, 1997, SYNLETT, P803

[15] NOVEL ALKYNE REACTIONS WITH BINUCLEAR MOLYBDENUM-SULFUR COMPLEXES - STRUCTURE OF THE DIMETHYL ACETYLENEDICARBOXYLATE ADDUCT OF [MO2O2(MU-S)2(S2)2]2- [J].

HALBERT, TR ;

PAN, WH ;

STIEFEL, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (16) :5476-5477

[16]

Han LB, 1999, CHEM LETT, P863

[17] Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes [J].

Han, LB ;

Zhang, C ;

Yazawa, H ;

Shimada, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5080-5081

[18] The first platinum(0)-catalyzed regio- and stereoselective thiosilylation of alkynes using disulfides and disilanes: A new strategy for introducing two different heteroatoms into carbon-carbon unsaturated bonds [J].

Han, LB ;

Tanaka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8249-8250

[19] Transition metal-catalysed addition reactions of H-heteroatom and inter-heteroatom bonds to carbon-carbon unsaturated linkages via oxidative additions [J].

Han, LB ;

Tanaka, M .

CHEMICAL COMMUNICATIONS, 1999, (05) :395-402

[20]

Herberhold M, 2000, CHEM-EUR J, V6, P3026, DOI 10.1002/1521-3765(20000818)6:16<3026::AID-CHEM3026>3.0.CO

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