Literature DB >> 29638130

Harnessing the β-Silicon Effect for Regioselective and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization by Donor/Acceptor Carbenes Derived from 1-Sulfonyl-1,2,3-triazoles.

Zachary J Garlets1, Huw M L Davies1.   

Abstract

The regioselective and enantioselective intermolecular sp3 C-H functionalization of silicon-substituted alkanes was accomplished using Rh2( S-NTTL)4 with readily available 1-sulfonyl-1,2,3-triazoles as carbene precursors. These reactions generate a diverse array of stereodefined substituted silaalkanes.

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Year:  2018        PMID： 29638130      PMCID： PMC6035867          DOI： 10.1021/acs.orglett.8b00427

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  30 in total

Review 1.  The synthesis of biologically active organosilicon small molecules.

Authors:  Annaliese K Franz
Journal:  Curr Opin Drug Discov Devel       Date:  2007-11

2.  Sila-substitution--a useful strategy for drug design?

Authors:  R Tacke; H Zilch
Journal:  Endeavour       Date:  1986       Impact factor: 0.444

3.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

Review 4.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

5.  Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation.

Authors:  Hongjuan Shen; Junkai Fu; Hao Yuan; Jianxian Gong; Zhen Yang
Journal:  J Org Chem       Date:  2016-05-24       Impact factor: 4.354

6.  One-pot synthesis of 2,3-disubstituted dihydrobenzofurans and benzofurans via rhodium-catalyzed intramolecular C-H insertion reaction.

Authors:  Xueji Ma; Feifei Wu; Xiaofei Yi; Hangxiang Wang; Wanzhi Chen
Journal:  Chem Commun (Camb)       Date:  2015-04-21       Impact factor: 6.222

7.  Stereodivergent Intramolecular C(sp(3))-H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N-Heterotricycles.

Authors:  Vincent N G Lindsay; Hélène M-F Viart; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

8.  Rhodium-Catalyzed Insertion of Carbenoids into beta C-H Bonds of Silacycloalkanes: A Facile and General Approach to Functionalized Silacycloalkanes.

Authors:  Yasuo Hatanaka; Masahiro Watanabe; Masato Tanaka; Hideki Sakurai
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

Review 9.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

10.  Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.

Authors:  Robert W Kubiak; Jeffrey D Mighion; Sidney M Wilkerson-Hill; Joshua S Alford; Tetsushi Yoshidomi; Huw M L Davies
Journal:  Org Lett       Date:  2016-06-22       Impact factor: 6.005
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  6 in total

1.  Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Organosilanes by Donor/Acceptor Carbenes Derived from Aryldiazoacetates.

Authors:  Zachary J Garlets; Elliot F Hicks; Jiantao Fu; Eric A Voight; Huw M L Davies
Journal:  Org Lett       Date:  2019-06-11       Impact factor: 6.005

2.  Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined β-Arylpyrrolidines.

Authors:  Robert W Kubiak; Huw M L Davies
Journal:  Org Lett       Date:  2018-06-21       Impact factor: 6.005

3.  Distal Allylic/Benzylic C-H Functionalization of Silyl Ethers Using Donor/Acceptor Rhodium(II) Carbenes.

Authors:  Janakiram Vaitla; Yannick T Boni; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-12       Impact factor: 15.336

4.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354

5.  Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.

Authors:  Alejandro Guarnieri-Ibáñez; Adiran de Aguirre; Céline Besnard; Amalia I Poblador-Bahamonde; Jérôme Lacour
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

6.  Blue light-promoted photolysis of aryldiazoacetates.

Authors:  Igor D Jurberg; Huw M L Davies
Journal:  Chem Sci       Date:  2018-05-22       Impact factor: 9.825
  6 in total

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