Literature DB >> 24079389

Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Zachary D Miller1, Wei Li, Tomás R Belderrain, John Montgomery.   

Abstract

Regioselective methods for allene hydrosilylation have been developed, with regioselectivity being governed primarily by the choice of metal. Alkenylsilanes are produced via nickel catalysis with larger N-heterocyclic carbene (NHC) ligands, and allylsilanes are produced via palladium catalysis with smaller NHC ligands. These complementary methods allow either regioisomeric product to be obtained with exceptional regiocontrol.

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Year:  2013        PMID： 24079389      PMCID： PMC3838997          DOI： 10.1021/ja407749w

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


  32 in total

1.  Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds.

Authors:  Ian Fleming; Asuncion Barbero; David Walter
Journal:  Chem Rev       Date:  1997-10-01       Impact factor: 60.622

2.  Directing group-controlled hydrosilylation: regioselective functionalization of alkyne.

Authors:  Yuuya Kawasaki; Youhei Ishikawa; Kazunobu Igawa; Katsuhiko Tomooka
Journal:  J Am Chem Soc       Date:  2011-12-05       Impact factor: 15.419

3.  Regioselective nickel-catalyzed reductive couplings of enones and allenes.

Authors:  Wei Li; Nan Chen; John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

4.  Sequential Pd-catalyzed asymmetric allene diboration/alpha-aminoallylation.

Authors:  Joshua D Sieber; James P Morken
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

5.  Silicon-based cross-coupling reaction: an environmentally benign version.

Authors:  Yoshiaki Nakao; Tamejiro Hiyama
Journal:  Chem Soc Rev       Date:  2011-07-14       Impact factor: 54.564

6.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

7.  Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.

Authors:  Barry M Trost; Zachary T Ball
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

8.  Enantioface-selective palladium-catalyzed silaboration of allenes via double asymmetric induction.

Authors:  Michinori Suginome; Toshimichi Ohmura; Yoshihiro Miyake; Shin'ichirou Mitani; Yoshihiko Ito; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

9.  Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.

Authors:  Jeremy Kister; Amy C DeBaillie; Ricardo Lira; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

10.  Origin of thermodynamic versus kinetic control of allene hydroboration with 9-borabicyclo[3.3.1]nonane and 10(R)-trimethylsilyl-9-borabicyclo[3.3.2]decane.

Authors:  Daniel H Ess; Jeremy Kister; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005
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  11 in total

1.  NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors:  Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2017-07-03       Impact factor: 15.419

2.  Exo-selective reductive macrocyclization of ynals.

Authors:  Hengbin Wang; Solymar Negretti; Allison R Knauff; John Montgomery
Journal:  Org Lett       Date:  2015-03-06       Impact factor: 6.005

3.  Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings.

Authors:  Evan P Jackson; Hasnain A Malik; Grant J Sormunen; Ryan D Baxter; Peng Liu; Hengbin Wang; Abdur-Rafay Shareef; John Montgomery
Journal:  Acc Chem Res       Date:  2015-05-12       Impact factor: 22.384

4.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

5.  Regioselective allene hydroarylation via one-pot allene hydrosilylation/Pd-catalyzed cross-coupling.

Authors:  Zachary D Miller; John Montgomery
Journal:  Org Lett       Date:  2014-10-02       Impact factor: 6.005

6.  Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Authors:  Evan P Jackson; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419

7.  Access to stereodefined (Z)-allylsilanes and (Z)-allylic alcohols via cobalt-catalyzed regioselective hydrosilylation of allenes.

Authors:  Chao Wang; Wei Jie Teo; Shaozhong Ge
Journal:  Nat Commun       Date:  2017-12-22       Impact factor: 14.919

8.  Cobalt-catalyzed regioselective stereoconvergent Markovnikov 1,2-hydrosilylation of conjugated dienes.

Authors:  Hui Leng Sang; Songjie Yu; Shaozhong Ge
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

9.  Biomimetic caged platinum catalyst for hydrosilylation reaction with high site selectivity.

Authors:  Ganghuo Pan; Chunhua Hu; Song Hong; Huaping Li; Dongdong Yu; Chengqian Cui; Qiaosheng Li; Nianjie Liang; Ying Jiang; Lirong Zheng; Lei Jiang; Yuzhou Liu
Journal:  Nat Commun       Date:  2021-01-04       Impact factor: 14.919

10.  Case Study of N-i Pr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2 ].

Authors:  Lukas Tendera; Moritz Helm; Mirjam J Krahfuss; Maximilian W Kuntze-Fechner; Udo Radius
Journal:  Chemistry       Date:  2021-11-16       Impact factor: 5.020
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