Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes

Xavier Guinchard; Xavier Bugaut; Cyril Cook; Emmanuel Roulland

doi:10.1002/chem.200900425

Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes

Chemistry - A European Journal ◽

10.1002/chem.200900425 ◽

2009 ◽

Vol 15 (23) ◽

pp. 5793-5798 ◽

Cited By ~ 27

Author(s):

Xavier Guinchard ◽

Xavier Bugaut ◽

Cyril Cook ◽

Emmanuel Roulland

Keyword(s):

Cross Coupling ◽

Trisubstituted Alkenes

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ChemInform Abstract: A Convenient Hydroiodination of Alkynes Using I2/PPh3/H2O and Its Application to the One-Pot Synthesis of Trisubstituted Alkenes via Iodoalkenes Using Pd-Catalyzed Cross-Coupling Reactions.

ChemInform ◽

10.1002/chin.201518042 ◽

2015 ◽

Vol 46 (18) ◽

pp. no-no

Author(s):

Shin-ichi Kawaguchi ◽

Yuhei Gonda ◽

Haruna Masuno ◽

Hue Thi Vu ◽

Kotaro Yamaguchi ◽

...

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

One Pot ◽

One Pot Synthesis ◽

Cross Coupling Reactions ◽

The One ◽

Trisubstituted Alkenes

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ChemInform Abstract: Synthesis of Exocyclic Trisubstituted Alkenes via Nickel-Catalyzed Kumada-Type Cross-Coupling Reaction of gem- Difluoroalkenes with Di-Grignard Reagents.

ChemInform ◽

10.1002/chin.201622068 ◽

2016 ◽

Vol 47 (22) ◽

Author(s):

Wenpeng Dai ◽

Xuxue Zhang ◽

Juan Zhang ◽

Yingyin Lin ◽

Song Cao

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Grignard Reagents ◽

Cross Coupling Reaction ◽

Trisubstituted Alkenes

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Synthesis of Exocyclic Trisubstituted Alkenes via Nickel‐ Catalyzed Kumada‐Type Cross‐Coupling Reaction of gem ‐ Difluoroalkenes with Di‐Grignard Reagents

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201500889 ◽

2016 ◽

Vol 358 (2) ◽

pp. 183-187 ◽

Cited By ~ 19

Author(s):

Wenpeng Dai ◽

Xuxue Zhang ◽

Juan Zhang ◽

Yingyin Lin ◽

Song Cao

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Grignard Reagents ◽

Cross Coupling Reaction ◽

Trisubstituted Alkenes

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Stereo- and Regiospecific Synthesis of Trisubstituted Alkenes via the Palladium-catalyzed Cross-coupling Reaction of Diisopropyl (E)-(1-Alkyl-1-alkenyl)boronates with Organic Halides

Chemistry Letters ◽

10.1246/cl.1986.1329 ◽

1986 ◽

Vol 15 (8) ◽

pp. 1329-1332 ◽

Cited By ~ 46

Author(s):

Makoto Satoh ◽

Norio Miyaura ◽

Akira Suzuki

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Cross Coupling Reaction ◽

Organic Halides ◽

Palladium Catalyzed ◽

Trisubstituted Alkenes

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Highly Stereo- and Regioselective Synthesis of (Z)-Trisubstituted Alkenes via 1-Bromo-1-alkyne Hydroboration−Migratory Insertion−Zn-Promoted Iodinolysis and Pd-Catalyzed Organozinc Cross-Coupling

Journal of the American Chemical Society ◽

10.1021/ja0772039 ◽

2007 ◽

Vol 129 (47) ◽

pp. 14788-14792 ◽

Cited By ~ 41

Author(s):

Zhihong Huang ◽

Ei-ichi Negishi

Keyword(s):

Cross Coupling ◽

Regioselective Synthesis ◽

Migratory Insertion ◽

Trisubstituted Alkenes

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Trisubstituted alkenes from alkynes and aryl iodides by boron-to-zinc transmetallation and palladium(0) catalysed cross coupling

Journal of Organometallic Chemistry ◽

10.1016/0022-328x(93)83047-y ◽

1993 ◽

Vol 444 (1-2) ◽

pp. 15-19 ◽

Cited By ~ 9

Author(s):

Konstantinos A. Agrios ◽

Morris Srebnik

Keyword(s):

Cross Coupling ◽

Aryl Iodides ◽

Trisubstituted Alkenes

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Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling

Organic Letters ◽

10.1021/ol901566e ◽

2009 ◽

Vol 11 (18) ◽

pp. 4092-4095 ◽

Cited By ~ 70

Author(s):

Chao Wang ◽

Tomas Tobrman ◽

Zhaoqing Xu ◽

Ei-ichi Negishi

Keyword(s):

Stereoselective Synthesis ◽

Cross Coupling ◽

Trisubstituted Alkenes

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A regio- and stereoselective entry to (Z)-β-halo alkenyl sulfides and their applications to access stereodefined trisubstituted alkenes

Organic & Biomolecular Chemistry ◽

10.1039/c4ob00103f ◽

2014 ◽

Vol 12 (14) ◽

pp. 2310-2321 ◽

Cited By ~ 20

Author(s):

Ge Liu ◽

Lichun Kong ◽

Ji Shen ◽

Gangguo Zhu

Keyword(s):

Stereoselective Synthesis ◽

Cross Coupling ◽

Trisubstituted Alkenes ◽

New Entry

A regio- and stereoselective synthesis of (Z)-β-halo alkenyl sulfides via K2CO3-promoted hydrothiolation of haloalkynes has been reported, permitting a new entry to trisubstituted alkenes featuring the iterative cross-coupling of carbon–halide and carbon–sulfur bonds.

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