硝酸铈铵催化下的烯丙基芳醚选择性碘代和溴代反应

Selective iodination and bromination of allyl aryl ether with iodine or bromine in the presence of ceric ammonium nitrate

以硝酸铈铵I2/CAN为反应体系时,当苯环上有给电子基团,碘和硝酸根对烯丙基双键的加成及苯环单碘代产物,收率较好;当苯环连有吸电子基团时,碘和硝酸根对烯丙基双键加成,产率较低.以Br2/CAN为反应体系时,当苯环上连有给电子基团时,溴对烯丙基碳碳双键加成,苯环上发生了一溴代或二溴代,产率中等;当苯环上连有吸电子基团时,溴对烯丙基碳碳双键加成,产率较高.

Molecular iodine in the presence of CAN has been utilized efficiently for iodonitration of C-C double bond and selective iodination of allyl aryl ether bearing electron donating group and for only iodonitration of C-C double bond of allyl aryl ether bearing electron withdrawing group under mild reaction conditions in mild to high yields. Molecular bromine in the presence of CAN has been utilized efficiently for dibromination of C-C double bond and selective bromination of allyl aryl ether bearing electron donating group and for only dibromination of C-C double bond of allyl aryl ether bearing electron withdrawing group under mild reaction conditions in mild to high yields.