Literature DB >> 26322957

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Jillian E Spangler1, Yoshihisa Kobayashi2, Pritha Verma1, Dong-Hui Wang1, Jin-Quan Yu1.   

Abstract

Pd(II)-catalyzed α-C(sp(3))-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.

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Year:  2015        PMID： 26322957      PMCID： PMC4822695          DOI： 10.1021/jacs.5b06740

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  51 in total

1.  Phosphoramidate tantalum complexes for room-temperature C-H functionalization: hydroaminoalkylation catalysis.

Authors:  Pierre Garcia; Ying Yin Lau; Mitchell R Perry; Laurel L Schafer
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-23       Impact factor: 15.336

2.  Ir(I)-catalyzed enantioselective secondary sp3 C-H bond activation of 2-(alkylamino)pyridines with alkenes.

Authors:  Shiguang Pan; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

3.  Direct functionalization of tetrahydrofuran and 1,4-dioxane: nickel-catalyzed oxidative C(sp3)-H arylation.

Authors:  Dong Liu; Chao Liu; Heng Li; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-19       Impact factor: 15.336

4.  Ruthenium(II)-catalyzed C(sp3)-H α-alkylation of pyrrolidines.

Authors:  Marvin Schinkel; Lianhui Wang; Kris Bielefeld; Lutz Ackermann
Journal:  Org Lett       Date:  2014-03-18       Impact factor: 6.005

5.  Ru(3)(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes.

Authors:  N Chatani; T Asaumi; S Yorimitsu; T Ikeda; F Kakiuchi; S Murai
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

6.  2-Pyridonate tantalum complexes for the intermolecular hydroaminoalkylation of sterically demanding alkenes.

Authors:  Eugene Chong; Jason W Brandt; Laurel L Schafer
Journal:  J Am Chem Soc       Date:  2014-07-23       Impact factor: 15.419

7.  Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Authors:  Graeme Barker; Julia L McGrath; Artis Klapars; Darren Stead; George Zhou; Kevin R Campos; Peter O'Brien
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

8.  Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors:  Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal:  Isr J Chem       Date:  2010-12       Impact factor: 3.333

9.  Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.

Authors:  Graeme Barker; Peter O'Brien; Kevin R Campos
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

10.  Simple and sustainable iron-catalyzed aerobic C-H functionalization of N,N-dialkylanilines.

Authors:  Maxim O Ratnikov; Xinfang Xu; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419
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  24 in total

1.  Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors:  Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal:  Chem Rev       Date:  2016-12-02       Impact factor: 60.622

2.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

3.  Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors:  Anh T Tran; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-24       Impact factor: 15.336

4.  Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

Authors:  Melissa Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2017-01-17       Impact factor: 6.005

5.  Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination.

Authors:  Kwangmin Shin; Yoonsu Park; Mu-Hyun Baik; Sukbok Chang
Journal:  Nat Chem       Date:  2017-12-11       Impact factor: 24.427

6.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

7.  Direct α-C-H bond functionalization of unprotected cyclic amines.

Authors:  Weijie Chen; Longle Ma; Anirudra Paul; Daniel Seidel
Journal:  Nat Chem       Date:  2017-11-06       Impact factor: 24.427

8.  Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group.

Authors:  Yongwei Wu; Yan-Qiao Chen; Tao Liu; Martin D Eastgate; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-11-01       Impact factor: 15.419

9.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

10.  Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles.

Authors:  Pritha Verma; Jeremy M Richter; Nikita Chekshin; Jennifer X Qiao; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-03-09       Impact factor: 15.419
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