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Synlett 2011(15): 2253-2255  
DOI: 10.1055/s-0030-1261193
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Carbonylation of Aryl and Heteroaryl Bromides under Atmospheric Pressure of CO

Weizhun Yanga,b, Wei Han*a, Weidong Zhangc, Lei Shan*c, Jiansong Sun*b
a School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
e-Mail: jssun@sioc.ac.cn;
c Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China
Further Information

Publication History

Received 30 April 2011
Publication Date:
24 August 2011 (online)

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Abstract

In the presence of Et3N and n-BuOH, efficient alkoxycarbonylation of (hetero)aromatic bromides was achieved under atmospheric pressure of carbon monoxide with in situ generated palladium/rac-BINAP as catalyst.

Key words

palladium catalyst - cross-coupling - atmospheric pressure - carbonylation - alkoxycarbonylation

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Representative Procedure A stirred solution of 7-bromoisoquinoline (62 mg, 0.3 mmol) and Et3N (0.07 mL, 0.45 mmol) in n-BuOH (1 mL) was treated with PdCl2 (1 mg, 2 mol%) and rac-BINAP (7 mg, 4 mol%). The reaction mixture was degassed and refilled with CO (balloon) for three times, and then stirred for 12 h at 120 ˚C. Solvent was removed under reduced pressure, and the resulting residue was purified by column chromatography to provide butyl isoquinoline-7-carboxylate in 96% yield (66 mg).