Literature DB >> 16601184

C-H bond functionalization in complex organic synthesis.

Kamil Godula1, Dalibor Sames.   

Abstract

Direct and selective replacement of carbon-hydrogen bonds with new bonds (such as C-C, C-O, and C-N) represents an important and long-standing goal in chemistry. These transformations have broad potential in synthesis because C-H bonds are ubiquitous in organic substances. At the same time, achieving selectivity among many different C-H bonds remains a challenge. Here, we focus on the functionalization of C-H bonds in complex organic substrates catalyzed by transition metal catalysts. We outline the key concepts and approaches aimed at achieving selectivity in complex settings and discuss the impact these reactions have on synthetic planning and strategy in organic synthesis.

Entities:  

Year:  2006        PMID: 16601184     DOI: 10.1126/science.1114731

Source DB:  PubMed          Journal:  Science        ISSN: 0036-8075            Impact factor:   47.728


  165 in total

1.  Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

Authors:  Lei Bi; Gunda I Georg
Journal:  Org Lett       Date:  2011-09-22       Impact factor: 6.005

2.  C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors:  Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

3.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

4.  Direct arylation of 6-phenylpurine and 6-arylpurine nucleosides by ruthenium-catalyzed C-H bond activation.

Authors:  Mahesh K Lakshman; Ashoke C Deb; Raghu Ram Chamala; Padmanava Pradhan; Ramendra Pratap
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-28       Impact factor: 15.336

5.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

6.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

7.  Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction.

Authors:  Xixi Song; Aiguo Song; Fang Zhang; He-Xing Li; Wei Wang
Journal:  Nat Commun       Date:  2011-11-08       Impact factor: 14.919

8.  Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

9.  Activation of sp3 C-H bonds with cobalt(I): catalytic synthesis of enamines.

Authors:  Andrew D Bolig; Maurice Brookhart
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

10.  A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds.

Authors:  Andrew M Sawayama; Michael M Y Chen; Palaniappan Kulanthaivel; Ming-Shang Kuo; Horst Hemmerle; Frances H Arnold
Journal:  Chemistry       Date:  2009-11-02       Impact factor: 5.236

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