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Efficient C-B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal- Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic r,-Unsaturated Carbonyls [J. Am. Chem. Soc. 2009, 131, 7253–7255]. Kang-sang Lee, Adil R. Zhugralin, and Amir H. Hoveyda* Scheme 2 and related discussion. The 11 B NMR data originally reported for the NHC · 5 complex are incorrect. The correct values (THF-d 8 , -10 °C) are for signals at δ 1.8 (sp 3 B) and 36.3 (sp 2 B), which appear as broad peaks (slow and reversible complexation on the NMR time scale). The signals for NHC · 4 are too weak to measure accurately since, as described in the manuscript, the complex formation is inefficient (large amounts of B 2 (pin) 2 remain unreacted). The originally reported values correspond to minor impurities in the sample. JA107037R 10.1021/ja107037r Published on Web 08/16/2010 10.1021/ja107037r 2010 American Chemical Society 12766 9 J. AM. CHEM. SOC. 2010, 132, 12766

Efficient C−B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions

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Page 1: Efficient C−B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions

Efficient C-B Bond Formation Promoted byN-Heterocyclic Carbenes: Synthesis of Tertiary andQuaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclicand Acyclic r,�-Unsaturated Carbonyls [J. Am.Chem. Soc. 2009, 131, 7253–7255]. Kang-sang Lee,Adil R. Zhugralin, and Amir H. Hoveyda*

Scheme 2 and related discussion. The 11B NMR dataoriginally reported for the NHC ·5 complex are incorrect. Thecorrect values (THF-d8, -10 °C) are for signals at δ 1.8 (sp3

B) and 36.3 (sp2 B), which appear as broad peaks (slow andreversible complexation on the NMR time scale). The signalsfor NHC ·4 are too weak to measure accurately since, asdescribed in the manuscript, the complex formation is inefficient(large amounts of B2(pin)2 remain unreacted). The originallyreported values correspond to minor impurities in the sample.

JA107037R

10.1021/ja107037rPublished on Web 08/16/2010

10.1021/ja107037r 2010 American Chemical Society12766 9 J. AM. CHEM. SOC. 2010, 132, 12766