Abstract
This chapter describes carbon-carbon bond formation mediated by organochromium compounds, especially nucleophilic addition of the organochromiums to carbonyl compounds. The chapter covers the major advances in this field after the publication of the first edition of Comprehensive Organic Synthesys (ORS1) in 1991, and consists of three sections: (1) Formation of carbon-carbon single bond with allyl-, propargyl-, alkenyl-, aryl-, and alkynylchromium compounds: These compounds are prepared by reduction of the corresponding halides with chromium(II), and the latter three compounds requires to conduct under nickel catalysis. The carbonyl addition proceed under mild conditions in a regio-, stereo-, and chemoselective manner. (2) Formation of carbon-carbon double bonds with geminal dichromium reagents: The reagents are generated from geminal haloalkanes and chromium(II), and add to aldehydes to give E-alkenes stereoselectively. The reaction also proceed under mild conditions chemoselectively. (3) Miscellaneous carbon-carbon bond formation with other organochromium compounds. Examples of the organochromium reagents for natural product syntheses are shown in each section.
| Original language | English |
|---|---|
| Title of host publication | Comprehensive Organic Synthesis: Second Edition |
| Publisher | Elsevier Ltd. |
| Pages | 159-203 |
| Number of pages | 45 |
| Volume | 1 |
| ISBN (Print) | 9780080977430 |
| DOIs | |
| Publication status | Published - Feb 2014 |
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Keywords
- E-iodoalkene
- E-olefination
- Geminal dichromium
- Nickel catalysis
- Nozaki-Hiyama-Kishi reaction
- Organochromium
- Takai reaction
ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)
Cite this
Organochromium Reagents. / Takai, Kazuhiko.
Comprehensive Organic Synthesis: Second Edition. Vol. 1 Elsevier Ltd., 2014. p. 159-203.Research output: Chapter in Book/Report/Conference proceeding › Chapter
}
TY - CHAP
T1 - Organochromium Reagents
AU - Takai, Kazuhiko
PY - 2014/2
Y1 - 2014/2
N2 - This chapter describes carbon-carbon bond formation mediated by organochromium compounds, especially nucleophilic addition of the organochromiums to carbonyl compounds. The chapter covers the major advances in this field after the publication of the first edition of Comprehensive Organic Synthesys (ORS1) in 1991, and consists of three sections: (1) Formation of carbon-carbon single bond with allyl-, propargyl-, alkenyl-, aryl-, and alkynylchromium compounds: These compounds are prepared by reduction of the corresponding halides with chromium(II), and the latter three compounds requires to conduct under nickel catalysis. The carbonyl addition proceed under mild conditions in a regio-, stereo-, and chemoselective manner. (2) Formation of carbon-carbon double bonds with geminal dichromium reagents: The reagents are generated from geminal haloalkanes and chromium(II), and add to aldehydes to give E-alkenes stereoselectively. The reaction also proceed under mild conditions chemoselectively. (3) Miscellaneous carbon-carbon bond formation with other organochromium compounds. Examples of the organochromium reagents for natural product syntheses are shown in each section.
AB - This chapter describes carbon-carbon bond formation mediated by organochromium compounds, especially nucleophilic addition of the organochromiums to carbonyl compounds. The chapter covers the major advances in this field after the publication of the first edition of Comprehensive Organic Synthesys (ORS1) in 1991, and consists of three sections: (1) Formation of carbon-carbon single bond with allyl-, propargyl-, alkenyl-, aryl-, and alkynylchromium compounds: These compounds are prepared by reduction of the corresponding halides with chromium(II), and the latter three compounds requires to conduct under nickel catalysis. The carbonyl addition proceed under mild conditions in a regio-, stereo-, and chemoselective manner. (2) Formation of carbon-carbon double bonds with geminal dichromium reagents: The reagents are generated from geminal haloalkanes and chromium(II), and add to aldehydes to give E-alkenes stereoselectively. The reaction also proceed under mild conditions chemoselectively. (3) Miscellaneous carbon-carbon bond formation with other organochromium compounds. Examples of the organochromium reagents for natural product syntheses are shown in each section.
KW - E-iodoalkene
KW - E-olefination
KW - Geminal dichromium
KW - Nickel catalysis
KW - Nozaki-Hiyama-Kishi reaction
KW - Organochromium
KW - Takai reaction
UR - http://www.scopus.com/inward/record.url?scp=84903495494&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84903495494&partnerID=8YFLogxK
U2 - 10.1016/B978-0-08-097742-3.00108-7
DO - 10.1016/B978-0-08-097742-3.00108-7
M3 - Chapter
AN - SCOPUS:84903495494
SN - 9780080977430
VL - 1
SP - 159
EP - 203
BT - Comprehensive Organic Synthesis: Second Edition
PB - Elsevier Ltd.
ER -