Palladium catalyzed addition of carbon pronucleophiles to conjugated enynes

被引：21

作者：

Gevorgyan, V

Kadowaki, C

Salter, MM

Kadota, I

Saito, S

Yamamoto, Y

机构：

[1] TOHOKU UNIV,GRAD SCH SCI,DEPT CHEM,SENDAI,MIYAGI 98077,JAPAN

[2] TOHOKU UNIV,INST CHEM REACT SCI,RES CTR ORGAN RESOURCES & MAT CHEM,SENDAI,MIYAGI 98077,JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 27期

关键词：

D O I：

10.1016/S0040-4020(97)00602-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium catalyzed addition of certain carbon pronucleophiles 2 to conjugated enynes 1 afforded the corresponding allenes 3 in good to excellent yields. The most reactive methynes such as methylmalononitrile 2c enabled to undergo double addition leading to alkenes 4. Catalyst optimization supported Pd-2(dba)(3) . CHC3 - dppf combination as the best system among all catalysts tested. The plausible mechanisms for these catalytic reactions were proposed. (C) 1997 Elsevier Science Ltd.

引用

页码：9097 / 9106

页数：10

共 20 条

[1] Michael reaction of stabilized carbon nucleophiles catalyzed by [RuH2(PPh(3))(4)]
GomezBengoa, E
Cuerva, JM
Mateo, C
Echavarren, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) : 8553 - 8565
[2] 5-METHYLADENINE - A TRANSIENT INTERMEDIATE IN A TRANSLOCATIVE REARRANGEMENT
HOSMANE, RS
BAKTHAVACHALAM, V
LEONARD, NJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) : 235 - 239
[3] KLEIJN H, 1983, RECL TRAV CHIM PAY B, V102, P378
[4] REGIOSPECIFIC FUNCTIONALIZATION OF DIMETALLATED ISOPROPENYLACETYLENE, A SYNTHETIC EQUIVALENT OF THE ISOPRENE ANION - AN EFFICIENT SYNTHESIS OF THE BARK BEETLE PHEROMONES (+/-)-IPSENOL AND (+/-)-IPSDIENOL
KLUSENER, PAA
KULIK, W
BRANDSMA, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) : 5261 - 5266
[5] Knochel P., 1991, COMPREHENSIVE ORGANI, V4, P865
[6] PALLADIUM(0)-CATALYZED HYDROBORATION OF 1-BUTEN-3-YNES - PREPARATION OF ALLENYLBORANES
MATSUMOTO, Y
NAITO, M
HAYASHI, T
[J]. ORGANOMETALLICS, 1992, 11 (07) : 2732 - 2734
[7] RUTHENIUM-CATALYZED ALDOL AND MICHAEL REACTIONS OF ACTIVATED NITRILES
NAOTA, T
TAKI, H
MIZUNO, M
MURAHASHI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) : 5954 - 5955
[8] BIMETALLIC CATALYTIC-SYSTEMS CONTAINING TI, ZR, NI, AND PD - THEIR APPLICATIONS TO SELECTIVE ORGANIC SYNTHESES
NEGISHI, E
[J]. PURE AND APPLIED CHEMISTRY, 1981, 53 (12) : 2333 - 2356
[9] PREPARATION OF METHYL 1,3-DIEN-2-CARBOXYLATE BY THE PALLADIUM-CATALYZED CARBONYLATION OF 2,3-DIEN-1-OLS
NOKAMI, J
MAIHARA, A
TSUJI, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5629 - 5630
[10] RHODIUM-CATALYZED MICHAEL ADDITIONS OF ACTIVATED NITRILES TO ALPHA,BETA-UNSATURATED ESTERS
PAGANELLI, S
SCHIONATO, A
BOTTEGHI, C
[J]. TETRAHEDRON LETTERS, 1991, 32 (24) : 2807 - 2810

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