Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides

The Journal of Organic Chemistry
Andrew J RossRichard F Jackson

Abstract

A combination of Pd(2)(dba)(3) and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield.

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Citations

Apr 10, 2010·Chemical Communications : Chem Comm·Tobias D BlümkePaul Knochel
Dec 30, 2015·ACS Medicinal Chemistry Letters·Aaron M BenderHenry I Mosberg
Jul 9, 2014·Chemical Communications : Chem Comm·Matthew LilleyRichmond Muimo
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Feb 6, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Michelle MontgomeryRobin B Bedford
Aug 30, 2011·Organic & Biomolecular Chemistry·Sara KenisNorbert De Kimpe
Feb 2, 2011·Organic & Biomolecular Chemistry·Neil ColginSteven L Cobb
Dec 5, 2017·Organic & Biomolecular Chemistry·William D G Brittain, Steven L Cobb
Jun 9, 2020·Beilstein Journal of Organic Chemistry·Laila Fathy Awad, Mohammed Salah Ayoup
Jul 28, 2016·Bioorganic & Medicinal Chemistry·Aaron L Featherston, Scott J Miller
Mar 30, 2010·Organic Letters·Vinson R Espejo, Jon D Rainier
Nov 12, 2010·The Journal of Organic Chemistry·Ahmad Reza MassahRichard F W Jackson
Sep 20, 2011·The Journal of Organic Chemistry·Laurin MelzigPaul Knochel
Mar 21, 2019·The Journal of Organic Chemistry·Jung-Ah ShinHee-Yoon Lee
Dec 7, 2013·Organic Letters·Benjamin N RockeAndrei Shavnya
Aug 9, 2017·The Journal of Organic Chemistry·Qiang LiuYun He
Jul 11, 2019·Organic Letters·Amira H DardirChristopher R Shugrue
May 29, 2018·The Journal of Organic Chemistry·Seyma OzturkMohammad R Seyedsayamdost
Oct 2, 2021·Chemical Communications : Chem Comm·Luke J DowmanRichard J Payne
Oct 30, 2021·Chemistry : a European Journal·Steffen DachwitzNorbert Sewald

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