Cobalt-catalyzed intermolecular stereoselective bisbenzylation of alkynes

被引：8

作者：

Komeyama, Kimihiro ^{[1
]}

Asakura, Ryota ^{[1
]}

Fukuoka, Hiroshi ^{[1
]}

Takaki, Ken ^{[1
]}

机构：

[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima, Hiroshima 7398527, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 13期

关键词：

Cobalt catalyst; Bisbenzylation; Carbocobaltation; Alkynes; Benzyl bromides; CARBON BOND FORMATION; O-IODOPHENYL KETONES; SELECTIVE SYNTHESIS; REAGENTS; ROUTE; CARBOCYCLIZATION; IRON;

D O I：

10.1016/j.tetlet.2015.02.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CoBr2/P(OMe)Ph-2 is found to be an effective catalyst-system for intermolecular bisbenzylation of allcynes with various benzyl bromides in the presence of manganese reductant. The transformation can be carried out under mild conditions, giving rise to stereocontrolled cis-1,2-bisbenzylated alkenes in good yields. (C) 2015 Published by Elsevier Ltd.

引用

页码：1735 / 1737

页数：3

共 39 条

[1] Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides
Amatore, Muriel
Gosmini, Corinne
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) : 5848 - 5852
[2] Total synthesis of (±) maculalactone A, maculalactone B and maculalactone C and the determination of the absolute configuration of natural (+) maculalactone A by asymmetric synthesis
Brown, GD
Wong, HF
[J]. TETRAHEDRON, 2004, 60 (25) : 5439 - 5451
[3] Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes
Chang, KJ
Rayabarapu, DK
Cheng, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) : 4781 - 4787
[4] Cobalt-catalyzed carbocyclization of o-Iodobenzaldehydes and o-Iodophenyl ketones with alkynes
Chang, KJ
Rayabarapu, DK
Cheng, CH
[J]. ORGANIC LETTERS, 2003, 5 (21) : 3963 - 3966
[5] Cobalt-catalysed synthesis of highly substituted styrene derivatives via arylzincation of alkynes
Corpet, Martin
Gosmini, Corinne
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (94) : 11561 - 11563
[6] New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust
Fillon, H
Gosmini, C
Périchon, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) : 3867 - 3870
[7] Stereocontrolled synthesis of tetrasubstituted olefins
Flynn, Alison B.
Ogilvie, William W.
[J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4698 - 4745
[8] ALKYLCOBALT CARBONYLS .7. (ETA-1-BENZYL)COBALT, (ETA-3-BENZYL)COBALT, AND (ETA-1-PHENYLACETYL)COBALT CARBONYLS
GALAMB, V
PALYI, G
UNGVARY, F
MARKO, L
BOESE, R
SCHMID, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) : 3344 - 3351
[9] ETA-1-BENZYLCOBALT AND ETA-3-BENZYLCOBALT CARBONYLS
GALAMB, V
PALYI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (09) : 487 - 488
[10] Gerard C., 2010, CHEM REV, V110, P1435

← 1 2 3 4 →