INVESTIGADORES
DORN Viviana
artículos
Título:
Phenols as starting materials for the synthesis of arilstannanes via SRN1
Autor/es:
B CHOPA, ALICIA; M. T. LOCKHART; V. B. DORN
Revista:
ORGANOMETALLICS
Editorial:
American Chemical Society
Referencias:
Lugar: Washington; Año: 2002 vol. 21 p. 1425 - 1429
ISSN:
0276-7333
Resumen:
Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with
sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford
arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP
(3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP
(7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in
fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups
react with 1 under irradiation, affording the corresponding di- or tristannylated aryl
compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate
(21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the
di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)
benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are
obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in
quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords
1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the
results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1,
as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.