Heck-type reactions of allylic alcohols -: Part IV:: (2-Substituted)-1-indanones via 5-endo-trig cyclizations

被引：22

作者：

Zawisza, Anna Maria ^{[1
]}

Ganchegui, Benjamin ^{[1
]}

Gonzalez, Ivan ^{[1
,2
]}

Bouquillon, Sandrine ^{[1
]}

Roglans, Anna ^{[2
]}

Henin, Francoise ^{[1
]}

Muzart, Jacques ^{[1
]}

机构：

[1] Univ Reims, CNRS, UMR React Select & Applicat, F-51687 Reims 2, France

[2] Univ Girona, Dept Chem, Girona, Spain

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2008年 / 283卷 / 1-2期

关键词：

palladium; catalysis; heck reaction; cyclization; allylic alcohol; DMF; cinchonine; microwaves;

D O I：

10.1016/j.molcata.2007.12.021

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Various conditions have been tested to obtain efficiently 2-methyl-1-indanone via the Pd-catalyzed 5-endo-trig cyclization of 1-(o-bromophenyl)2-methylprop-2-en-1-ol. High yield (97%) was obtained at 120 degrees C in DMF with Pd(OAc)(2)/cinchonine as the catalytic system and NaHCO3 as the base. Use of this procedure for the synthesis of other substituted indanones led to lower yields but replacing thermal heating by microwave heating improved greatly the results. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：140 / 145

页数：6

共 5 条

[1] Nucleophilic Phosphine-Catalyzed Intramolecular Michael Reactions of N-Allylic Substituted α-Amino Nitriles: Construction of Functionalized Pyrrolidine Rings via 5-endo-trig Cyclizations
En, Da
Zou, Gong-Feng
Guo, Yuan
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JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4456 - 4462
[2] Synthesis of 2-Substituted Indoles and Indolines via Suzuki-Miyaura Coupling/5-endo-trig Cyclization Strategies
Fuwa, Haruhiko
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JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01): : 212 - 221
[3] Heck-type 5-endo-trig cyclizations promoted by vinylic fluorines:: Ring-fluorinated indene and 3H-pyrrole syntheses from 1,1-difluoro-1-alkenes
Ichikawa, Junji
Sakoda, Kotaro
Mihara, Jun
Ito, Naotaka
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) : 489 - 504
[4] 5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes:: synthesis of 4-difluoromethylene-substituted 1-pyrrolines
Ichikawa, Junji
Nadano, Ryo
Ito, Naotaka
CHEMICAL COMMUNICATIONS, 2006, (42) : 4425 - 4427
[5] A NEW APPROACH TO 5-ARYLPYRROLIDIN-2-ONES VIA 5-ENDO-TRIG RADICAL CYCLIZATION OF ALPHA-HALO-SUBSTITUTED OR ALPHA-THIO-SUBSTITUTED N-(1-ARYLETHENYL)ACETAMIDES
SATO, T
MACHIGASHIRA, N
ISHIBASHI, H
IKEDA, M
HETEROCYCLES, 1992, 33 (01) : 139 - 142

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