Literature DB >> 21298176

C-H functionalization logic in total synthesis.

Will R Gutekunst1, Phil S Baran.   

Abstract

In this critical review, the strategic and economic benefits of C-H functionalization logic will be analyzed through the critical lens of total synthesis. In order to illustrate the dramatically simplifying effects this type of logic can potentially have on synthetic planning, we take the reader through a series of case studies in which it has already been successfully applied. In the first section, a chronological look at key historical syntheses will be examined, leading into modern day examples. In the second section, our own experience with applying and executing synthesis with a C-H functionalization "mindset" will be discussed (114 references).

Year:  2011        PMID: 21298176     DOI: 10.1039/c0cs00182a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  157 in total

1.  Function and Structure of MalA/MalA', Iterative Halogenases for Late-Stage C-H Functionalization of Indole Alkaloids.

Authors:  Amy E Fraley; Marc Garcia-Borràs; Ashootosh Tripathi; Dheeraj Khare; Eduardo V Mercado-Marin; Hong Tran; Qingyun Dan; Gabrielle P Webb; Katharine R Watts; Phillip Crews; Richmond Sarpong; Robert M Williams; Janet L Smith; K N Houk; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-08-21       Impact factor: 15.419

2.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

3.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

4.  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

5.  An enzymatic platform for the asymmetric amination of primary, secondary and tertiary C(sp3)-H bonds.

Authors:  Yang Yang; Inha Cho; Xiaotian Qi; Peng Liu; Frances H Arnold
Journal:  Nat Chem       Date:  2019-10-14       Impact factor: 24.427

6.  Enantioselective Total Synthesis of Nigelladine A via Late-Stage C-H Oxidation Enabled by an Engineered P450 Enzyme.

Authors:  Steven A Loskot; David K Romney; Frances H Arnold; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-07-24       Impact factor: 15.419

7.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

8.  The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  Org Lett       Date:  2012-12-19       Impact factor: 6.005

9.  Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

Authors:  Kevin Hung; Matthew L Condakes; Takahiro Morikawa; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2016-12-16       Impact factor: 15.419

10.  Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

Authors:  Laura K G Ackerman; Jesus I Martinez Alvarado; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2018-10-16       Impact factor: 15.419

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