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Borylation of a Stable Primary Enamine
Author(s) -
Erker Gerhard,
Wingbermühle Doris,
Grehl Matthias,
Fröhlich Roland
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270725
Subject(s) - chemistry , enamine , dichloromethane , borylation , substituent , medicinal chemistry , stereochemistry , organic chemistry , catalysis , aryl , alkyl , solvent
The stable conjugated primary enamine 1,6‐diamino‐1,6‐diphenyl‐1,3,5‐hexatriene ( 2a ) was treated with 9‐borabicyclo‐[3.3.1]nonane. At 40°C in dichloromethane solution (18 h) only borylation at nitrogen was observed. With loss of dihydrogen a 9‐BBN substituent became attached to each enamine nitrogen. The N , N ′‐diborylated diaminohexatriene product 3 was characterized by X‐ray diffraction.