TY - JOUR
T1 - One-pot two-step oxidative cleavage of 1,2-arylalkenes to aryl ketones instead of arylaldehydes in an aqueous medium
T2 - A complementary approach to ozonolysis
AU - Sharma, Naina
AU - Sharma, Abhishek
AU - Kumar, Rakesh
AU - Shard, Amit
AU - Sinha, Arun K.
PY - 2010/11
Y1 - 2010/11
N2 - A new approach has been developed for a one-pot and selective oxidative cleavage of aryl- and 1,2-diarylalkenes leading to one-carbon shorter aryl ketones; thereby, providing a complementary approach to classical ozonolysis. The methodology was applicable to diverse aromatic and polyaromaticarylalkenes bearing electron-donating or -withdrawing groups on the aromatic ring. The protocol also provided a useful one-pot oxidative cleavage-condensation sequence, which could potentially have important applications in natural product total synthesis. A one-pot, two-step approach has been achieved for the oxidative cleavage of 1,2-disubstituted arylalkenes into the corresponding aryl ketones instead of arylaldehydes (see scheme; NIS = N-iodosuccinimide; CTAB = cetyltrimethylammonium bromide; PDC/TBHP = pyridinium dichromate/tert-butyl hydroperoxide). The methodology also led to a valuable one-pot oxidative cleavage-condensation reaction that has widespread utility in the total synthesis of natural products.
AB - A new approach has been developed for a one-pot and selective oxidative cleavage of aryl- and 1,2-diarylalkenes leading to one-carbon shorter aryl ketones; thereby, providing a complementary approach to classical ozonolysis. The methodology was applicable to diverse aromatic and polyaromaticarylalkenes bearing electron-donating or -withdrawing groups on the aromatic ring. The protocol also provided a useful one-pot oxidative cleavage-condensation sequence, which could potentially have important applications in natural product total synthesis. A one-pot, two-step approach has been achieved for the oxidative cleavage of 1,2-disubstituted arylalkenes into the corresponding aryl ketones instead of arylaldehydes (see scheme; NIS = N-iodosuccinimide; CTAB = cetyltrimethylammonium bromide; PDC/TBHP = pyridinium dichromate/tert-butyl hydroperoxide). The methodology also led to a valuable one-pot oxidative cleavage-condensation reaction that has widespread utility in the total synthesis of natural products.
KW - Alkenes
KW - Cleavage reactions
KW - Ketones
KW - Microwave chemistry
KW - Oxidation
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U2 - 10.1002/ejoc.201000672
DO - 10.1002/ejoc.201000672
M3 - Article
AN - SCOPUS:78349291905
SN - 1434-193X
SP - 6025
EP - 6032
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 31
ER -