A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: a superior alternative to the Cadiot-Chodkiewicz reaction.
A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs is described. This method, like the Cadiot-Chodkiewicz reaction, requires three steps for the synthesis of R(1)Ctbd1;CCtbd1;CR(2) from R(1)Ctbd1;CH, R(2)X, and HCtbd1;CH. However, the high "pair"-selectivity permitting high-yield production of the desired conjugated diynes without separation of symmetrical diynes promises to make the present protocol superior to the Cadiot-Chodkiewicz reaction in many cases.
Negishi
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Herbert C. Brown Laboratories, Purdue University, West Lafayette, Indiana 47907, USA. negishi@purdue.edu
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D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium; D015032:Zinc
D000480:Alkynes; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D010165:Palladium; D015032:Zinc