Diverse Reactivity of Zirconacyclocumulenes Derived from Coupling of Benzynezirconocenes with 1,3‐Butadiynes towards Acyl Cyanides: Synthesis of Indeno[2,1‐ b ]pyrroles or [3]Cumulenones | Zendy

Fu Xiaoping | Zendy; Chen Jingjin | Zendy; Li Guangyu | Zendy; Liu Yuanhong | Zendy

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Diverse Reactivity of Zirconacyclocumulenes Derived from Coupling of Benzynezirconocenes with 1,3‐Butadiynes towards Acyl Cyanides: Synthesis of Indeno[2,1‐ b ]pyrroles or [3]Cumulenones

Author(s) -

Fu Xiaoping,

Chen Jingjin,

Li Guangyu,

Liu Yuanhong

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200900951

Subject(s) - reactivity (psychology) , substituent , stereoselectivity , chemistry , cycloaddition , aryl , alkyl , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology

Versatility : Cycloaddition of carbamoyl cyanides to 1,3‐butadiynes via seven‐membered zirconacyclocumulenes yields dihydroindeno[2,1‐ b ]pyrroles (see scheme, right); a C(sp 2 )H bond on the aromatic substituent of the 1,3‐butadiyne reactant is activated in the process. In contrast, reactions with aryl or alkyl acyl cyanides provide a stereoselective route to cis ‐[3]cumulenones (left).

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