Show simple item record

dc.contributor.authorLou, Sha
dc.contributor.authorFu, Gregory C.
dc.date.accessioned2011-12-16T21:30:50Z
dc.date.available2011-12-16T21:30:50Z
dc.date.issued2010-04
dc.identifier.issn0078-6209
dc.identifier.urihttp://hdl.handle.net/1721.1/67713
dc.description.abstractProcedure: A. (5-Cyanopentyl)zinc(II) bromide (1). An oven-dried, 200-mL pear-shaped Schlenk flask equipped with a magnetic stirbar (egg shaped, 25.4 × 12.7 mm) and an argon line connected to the standard taper outer joint is purged with argon for 5 min. Zinc powder (9.80 g, 150 mmol, 1.50 equiv) (Note 1) is added through the open neck, and then the flask is capped with a rubber septum and heated in an oil bath under high vacuum (0.5 mmHg) at 70 °C for 30 min. Then, the flask is refilled with argon, and anhydrous 1,3-dimethyl-2-imidazolidinone (DMI; 100 mL) (Note 2) is added via syringe. Iodine (I2) (634 mg, 2.50 mmol, 0.0250 equiv) (Note 3) is added in one portion through the neck. The neck is re-capped with a rubber septum, and the reaction mixture is stirred at 70 °C in an oil bath until the red color fades (~5 min). 6-Bromohexanenitrile (13.2 mL, 100 mmol, 1.00 equiv) (Note 4) is added via syringe over 4 min, and the reaction mixture is stirred at 70 °C for 12 h. Then, the oil bath is removed, and the mixture is allowed to cool at rt for 1 h without stirring. During this time, the unreacted zinc powder settles at the bottom of the flask. The flask is equipped with a fritted filter tube of medium porosity capped with an oven-dried, 2-necked 250-mL round-bottom flask, and the supernatant solution is filtered under argon by inverting the set-up (Note 5). The resulting clear yellow solution is employed in the next step without further purification. 1H NMR spectroscopy is used to determine that the concentration of the alkylzinc solution is 0.72 M (Note 6). This organozinc solution can be stored under argon at 0-4 °C for up to 3 weeks without deterioration.en_US
dc.language.isoen_US
dc.publisherJohn Wiley & Sons, Inc.en_US
dc.relation.isversionofhttp://www.orgsyn.org/orgsyn/prep.asp?prep=v87p0330en_US
dc.rightsCreative Commons Attribution-Noncommercial-Share Alike 3.0en_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/3.0/en_US
dc.sourcejohansen@mit.eduen_US
dc.titleNickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary alpha-Bromo Amides with Alkylzinc Reagents: (S)-N-Benzyl-7-cyano-2-ethyl-N-phenylheptanamideen_US
dc.title.alternativeNickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary α-Bromo Amides with Alkylzinc Reagents: (S)-N-Benzyl-7-cyano-2-ethyl-N-phenylheptanamideen_US
dc.typeArticleen_US
dc.identifier.citationLou, Sha and Gregory C. Fu. "Nickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary alpha-Bromo Amides with Alkylzinc Reagents: (S)-N-Benzyl-7-cyano-2-ethyl-N-phenylheptanamide." Organic Syntheses, Vol. 87, p.330 (2010).en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.approverFu, Gregory C.
dc.contributor.mitauthorFu, Gregory C.
dc.contributor.mitauthorLou, Sha
dc.relation.journalOrganic Synthesesen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsLou, Sha; Fu, Gregory C.en_US
mit.licenseOPEN_ACCESS_POLICYen_US


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record