NAPHTHALENE-CATALYZED REDUCTIVE DESULFONYLATION WITH LITHIUM - ALKYLLITHIUMS FROM ALKYL PHENYL SULFONES

被引：27

作者：

GUIJARRO, D ^{[1
]}

YUS, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)76673-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of alkyl aryl sulfones 1 with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound [(PrCHO)-C-i, PhCHO, Et(2)CO, (CH2)(5)CO] or trimethylchlorosilane (Barbier-type conditions) in THF at temperatures ranging between -78 and 20 degrees C leads, after hydrolysis with water, to the expected coupling products, arising from the corresponding alkyllithium in situ generated, in 30-61% yields.

引用

页码：2965 / 2968

页数：4

共 44 条

[21] NAPHTHALENE-CATALYZED LITHIATION OF DIALKYL SULFATES - A NEW ROUTE FOR ORGANOLITHIUM REAGENTS
GUIJARRO, D
MANCHENO, B
YUS, M
[J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5597 - 5600
[22] NAPHTHALENE-CATALYZED LITHIATION OF ALLYLIC AND BENZYLIC MESYLATES - A NEW METHOD FOR ALLYL, METHALLYL, AND BENZYL LITHIUM
GUIJARRO, D
MANCHENO, B
YUS, M
[J]. TETRAHEDRON, 1992, 48 (22) : 4593 - 4600
[23] NAPHTHALENE-CATALYZED LITHIATION OF PHENONE IMINES IN THE PRESENCE OF CARBONYL-COMPOUNDS - PREPARATION OF 1,2-AMINOALCOHOLS
GUIJARRO, D
YUS, M
[J]. TETRAHEDRON, 1993, 49 (35) : 7761 - 7768
[24] TRANSITION-METAL PROMOTED REACTIONS .27. NICKEL(II) LITHIUM ALUMINUM-HYDRIDE MEDIATED REDUCTION OF CARBON SULFUR BONDS
HO, KM
LAM, CH
LUH, TY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) : 4474 - 4476
[25] SYNTHESES VIA VINYL SULFONES .22. A CHEMODIRECTED, TRIPLY CONVERGENT TOTAL SYNTHESIS OF D-(+)-CARBACYCLIN
HUTCHINSON, DK
FUCHS, PL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4755 - 4756
[26] CONVENIENT METHODS FOR THE PREPARATION OF VINYLIC AND ALLYLIC SULFONES FROM ALKENES
INOMATA, K
KOBAYASHI, T
SASAOKA, S
KINOSHITA, H
KOTAKE, H
[J]. CHEMISTRY LETTERS, 1986, (03) : 289 - 292
[27] AN IMPROVED VARIANT OF THE JULIA OLEFIN SYNTHESIS - REDUCTIVE ELIMINATION OF BETA-HYDROXY IMIDAZOLYL SULFONES BY SAMARIUM DIIODIDE
KENDE, AS
MENDOZA, JS
[J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7105 - 7108
[28] REDUCTIVE DESULFONYLATION OF PHENYL SULFONES BY SAMARIUM(II) IODIDE-HEXAMETHYLPHOSPHORIC TRIAMIDE
KUNZER, H
STAHNKE, M
SAUER, G
WIECHERT, R
[J]. TETRAHEDRON LETTERS, 1991, 32 (17) : 1949 - 1952
[29] PREPARATION OF 4-(2-DEUTERIO-2-PROPYL)ANISOLE THROUGH CATHODIC CLEAVAGE OF A SULFONE IN THE PRESENCE OF DEUTERIUM-OXIDE
LAMM, B
NILSSON, A
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (01): : 77 - 78
[30] LAMM B, 1972, TETRAHEDRON LETT, P1469

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