Literature DB >> 19308939

Palladium-catalyzed oxidative intermolecular difunctionalization of terminal alkenes with organostannanes and molecular oxygen.

Kaveri Balan Urkalan1, Matthew S Sigman.   

Abstract

A cationic palladium complex catalyzes the title transformations, which are thought to proceed via a pi-allyl or pi-benzyl intermediate. The regioselectivity of the reaction (1,2- or 1,1-difunctionalization) depends on the type of terminal double bond (conjugated or nonconjugated) in the substrate (see scheme) and appears to be controlled by the relative rates of beta-hydride elimination and transmetalation. DMA=dimethylacetamide, Tf=triflyl.

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Year:  2009        PMID： 19308939      PMCID： PMC2844705          DOI： 10.1002/anie.200900218

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  34 in total

1.  Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors:  O Löber; M Kawatsura; J F Hartwig
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

2.  Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

Authors:  Lopa V Desai; Melanie S Sanford
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 3.  Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors:  Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors:  Guosheng Liu; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

5.  Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol.

Authors:  Keith M Gligorich; Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

6.  Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: a profound influence of an o-phenol.

Authors:  Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

7.  Regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids.

Authors:  Chengxiang Zhou; Richard C Larock
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

8.  Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors:  Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

9.  New phenylpropenoids, bis(1-phenylethyl)phenols, bisquinolinone alkaloid, and anti-inflammatory constituents from Zanthoxylum integrifoliolum.

Authors:  Jih-Jung Chen; Po-Hou Chen; Chang-Hui Liao; Shi-Yu Huang; Ih-Sheng Chen
Journal:  J Nat Prod       Date:  2007-09-07       Impact factor: 4.050

10.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384
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  42 in total

1.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

2.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

Authors:  Manuel Orlandi; Margaret J Hilton; Eiji Yamamoto; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

3.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

4.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

6.  Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates.

Authors:  Vaneet Saini; Longyan Liao; Qiaofeng Wang; Ranjan Jana; Matthew S Sigman
Journal:  Org Lett       Date:  2013-09-18       Impact factor: 6.005

7.  Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols.

Authors:  Zhi-Min Chen; Margaret J Hilton; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-09-01       Impact factor: 15.419

8.  Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors:  Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

10.  Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419
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