叔丁氧基羰基哌嗪基苯并呋喃-甲酸乙酯的合成Synthesisof.PDFVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 2 期, 203～206 Chinese Journal of Organic Chemistry No. 2, 203～206 ·研究论文· 5-(4-叔丁氧基羰基哌嗪基)苯并呋喃-2- 甲酸乙酯的合成 * 封 静 王成云 周长凯 左虎进 沈永嘉 (华东理工大学结构可控先进功能材料及其制备教育部重点实验 精细化工研究所 上海 200237) 摘要 5-溴苯并呋喃-2- 甲酸乙酯与 4-叔丁氧基羰基哌嗪进行 Buchwald-Hartwig 偶联反应, 若催化剂是 Pd(OAc)2/ BINAP, 碱是 Cs CO , 则产物主要是 5-(4-叔丁氧基羰基哌嗪基)苯并呋喃-2- 甲酸乙酯, 转化率达 70%; 若催化剂是 2 3 Pd(dba) /P(t-Bu) , 碱是叔丁醇钾, 则产物中几乎没有 5-(4-叔丁氧基羰基哌嗪基)苯并呋喃-2- 甲酸乙酯. 文中讨论了影响 2 3 这个 Buchwald-Hartwig 偶联反应的因素. 关键词 哌嗪; 苯并呋喃; 甲酸乙酯; 合成; Buchwald-Hartwig 偶联 Synthesis of Ethyl 5-(4-tert-Butyloxycarbonyl-1-piperazinyl)benzofu- ran-2-carboxylate Feng, Jing Wang, Chengyun Zhou, Changkai Zuo, Hujin Shen, Yongjia* (Laboratory for Advanced Materials , Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237) Abstract Buchwald-Hartwig coupling reaction between ethyl 5-bromobenzofuran-2-carboxylate and tert-butyl piperazine-1-carboxylate was studied. When Pd(OAc)2/BINAP was employed as catalyst and Cs CO as base, the major reaction product was ethyl 5-(4-tert-butyloxycarbonyl-1-piperazinyl)benzofuran- 2 3 2-carboxylate, with a reaction conversion rate of 70%. While Pd(dba) /P(t-Bu) was employed as catalyst