Propargylic and allenic carbocycle synthesis through palladium-catalyzed dearomatization reaction

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2619-2627

  Peng, Bo ^a   Feng, Xiujuan ^a   Zhang, Xin ^a   Zhang, Sheng ^a   Bao, Ming ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL CHLORIDES; BENZYLIC; CARBOCYCLES; DEAROMATIZATION; EFFICIENT METHOD; ROOM TEMPERATURE;

CHLORINE COMPOUNDS; NAPHTHALENE; PALLADIUM;

SYNTHESIS (CHEMICAL);

BENZYL CHLORIDE DERIVATIVE; BENZYL DERIVATIVE; NAPHTHALENE DERIVATIVE; PALLADIUM; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DEAROMATIZATION; REACTION ANALYSIS; SYNTHESIS;

ALKADIENES; BENZENE; CATALYSIS; CHLORIDES; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 77951014822     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100211d     Document Type: Article

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55. This proposed mechanism is primarily based on the analogy of the allylative dearomatization (see ref 8). After our allylative deaaromatization paper appeared in 2001, Ariafared and Lin reported DFT studies on the mechanism of the allylative dearomatization, and the computational result suggested that an alternative mechanism would be more appropriate than our originally proposed mechanism (see: Ariafard, A.; Lin, Z. J. Am. Chem. Soc. 2006, 128, 13010-13016); ?-allyl-hapto-3-exo-benzyl palladium is a key intermediate, in which a 1,3-allyl migration from palladium to the C-4 position of the six-membered ring takes place to lead to the dearomatization product. We believe this is a plausible and interesting mechanism. We are not sure whether a similar 1,3-rearrangement easily takes place in the case of the allenyl-system. It is an interesting point whether such 1,3-rearrangement takes place equally or more easily in the ?-allenyl than in the ?-allyl palladium intermediate. Accordingly, there is possibility that a mechanism proposed by Ariafared and Lin may be operative in the present case