(PCy3)2Cl2Ru=CHPh Catalyzed Kharasch additions.: Application in a formal olefin carbonylation

被引：55

作者：

Lee, BT ^{[1
]}

Schrader, TO ^{[1
]}

Martín-Matute, B ^{[1
]}

Kauffman, CR ^{[1
]}

Zhang, P ^{[1
]}

Snapper, ML ^{[1
]}

机构：

[1] Boston Coll, Eugene F Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 34期

关键词：

Kharasch; metathesis; radical; carbonylation;

D O I：

10.1016/j.tet.2004.06.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(PCy3)(2)Cl2Ru=CHPh-catalyzed Kharasch additions of trihaloalkanes across olefins provide polyhalogenated adducts, which upon hydrolysis furnish alpha,beta-unsaturated ketones, aldehydes, or gamma-hydroxybutenolides. This two-step process represents an overall acylation or carbonylation of an olefin. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7391 / 7396

页数：6

共 46 条

[11] CONVENIENT SYNTHESIS OF THE 2-METHYL-4-HYDROXYBUT-2-ENOLIDE MOIETY OF STRIGOL [J].

COOPER, GK ;

DOLBY, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3414-3416

[12] Palladium-catalyzed highly diastereoselective cyclic carbopalladation-carbonylative esterification tandem reaction of iododienes and iodoarylalkenes [J].

Copéret, C ;

Negishi, E .

ORGANIC LETTERS, 1999, 1 (01) :165-167

[13] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[14] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

[15] A new class of ruthenium complexes containing Schiff base ligands as promising catalysts for atom transfer radical polymerization and ring opening metathesis polymerization [J].

De Clercq, B ;

Verpoort, F .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 180 (1-2) :67-76

[16]

de Silva E.D., 1980, TETRAHEDRON LETT, V21, P1611, DOI [10.1016/S0040-4039(00)77766-5, DOI 10.1016/S0040-4039(00)77766-5]

[17] Total synthesis and stereochemistry of (-)-cacospongionolide F [J].

Demeke, D ;

Forsyth, CJ .

ORGANIC LETTERS, 2003, 5 (07) :991-994

[18]

FARRAND JC, 1971, J ORG CHEM, V36, P3606

[19] Lewis acid-promoted Kharasch-Curran additions:: A competition kinetics study of bromine atom transfer addition of N-α-bromoacetyl-oxazolidinone to 1-hexene [J].

Feng, H ;

Kavrakova, IK ;

Pratt, DA ;

Tellinghuisen, J ;

Porter, NA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6050-6054

[20]

FREIDLINA R, 1979, IAN SSSR KH, P392

← 1 2 3 4 5 →