氧化偶联在复杂性构建转化中。
Oxidative Coupling in Complexity Building Transforms.
机构信息
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
出版信息
Acc Chem Res. 2017 Mar 21;50(3):638-643. doi: 10.1021/acs.accounts.6b00637.
Abstract
Since many synthetic targets in organic chemistry are larger, more functionalized, and more oxidized than the starting inputs used, methods that unite fragments with an increase in oxidation state possess inherent efficiencies. Thus, the potential for complexity building transforms by union of activated or unactivated C-H, N-H, or O-H centers is considerable, and the challenge lies in how to obtain selective reactions from any two of these centers.
摘要
由于有机化学中的许多合成目标都比起始输入物更大、更官能化和更氧化，因此具有增加氧化态的片段结合方法具有固有效率。因此，通过激活或未激活的 C-H、N-H 或 O-H 中心的结合来构建复杂性的潜力是相当大的，挑战在于如何从这两个中心中的任意两个获得选择性反应。
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本文引用的文献
1
Recent Advances in C-H Functionalization.
J Org Chem. 2016 Jan 15;81(2):343-50. doi: 10.1021/acs.joc.5b02818.
2
Evolution of C-H Bond Functionalization from Methane to Methodology.
J Am Chem Soc. 2016 Jan 13;138(1):2-24. doi: 10.1021/jacs.5b08707. Epub 2015 Dec 15.
3
Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations.
Chem Rev. 2015 Nov 25;115(22):12138-204. doi: 10.1021/cr500431s. Epub 2015 Nov 11.
4
Significant enhancement in the efficiency and selectivity of iron-catalyzed oxidative cross-coupling of phenols by fluoroalcohols.
Angew Chem Int Ed Engl. 2015 Mar 27;54(14):4198-202. doi: 10.1002/anie.201409694. Epub 2015 Feb 5.
5
Chemoselective activation of sp(3) vs sp(2) C-H bonds with Pd(II).
J Am Chem Soc. 2015 Jan 14;137(1):18-21. doi: 10.1021/ja5093166. Epub 2014 Dec 29.
6
Selective oxidative homo- and cross-coupling of phenols with aerobic catalysts.
J Am Chem Soc. 2014 May 14;136(19):6782-5. doi: 10.1021/ja500183z. Epub 2014 May 5.
7
The cross-dehydrogenative coupling of C(sp3)-H bonds: a versatile strategy for C-C bond formations.
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):74-100. doi: 10.1002/anie.201304268. Epub 2013 Nov 8.
8
Catalyst-controlled aliphatic C-H oxidations with a predictive model for site-selectivity.
J Am Chem Soc. 2013 Sep 25;135(38):14052-5. doi: 10.1021/ja407388y. Epub 2013 Sep 17.
9
Chemistry. Adding aliphatic C-H bond oxidations to synthesis.
Science. 2012 Feb 17;335(6070):807-9. doi: 10.1126/science.1207661.
10
Innate and guided C-H functionalization logic.
Acc Chem Res. 2012 Jun 19;45(6):826-39. doi: 10.1021/ar200194b. Epub 2011 Oct 21.
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