Organic chemistry: A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents

Tian Qin, Josep Cornella, Chao Li, Lara R. Malins, Jacob T. Edwards, Shuhei Kawamura, Brad D. Maxwell, Martin D. Eastgate, Phil S. Baran

Research output: Contribution to journalArticle

247 Citations (Scopus)

Abstract

Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (>70 examples).

Original languageEnglish (US)
Pages (from-to)801-805
Number of pages5
JournalScience
Volume352
Issue number6287
DOIs
StatePublished - May 13 2016
Externally publishedYes

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Organic Chemistry
Carboxylic Acids
Oxidation-Reduction
Esters
Nickel
Biological Products
Carbon Dioxide
Amides
Polymers
Water

ASJC Scopus subject areas

  • General

Cite this

Qin, T., Cornella, J., Li, C., Malins, L. R., Edwards, J. T., Kawamura, S., ... Baran, P. S. (2016). Organic chemistry: A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents. Science, 352(6287), 801-805. https://doi.org/10.1126/science.aaf6123

Organic chemistry : A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents. / Qin, Tian; Cornella, Josep; Li, Chao; Malins, Lara R.; Edwards, Jacob T.; Kawamura, Shuhei; Maxwell, Brad D.; Eastgate, Martin D.; Baran, Phil S.

In: Science, Vol. 352, No. 6287, 13.05.2016, p. 801-805.

Research output: Contribution to journalArticle

Qin, T, Cornella, J, Li, C, Malins, LR, Edwards, JT, Kawamura, S, Maxwell, BD, Eastgate, MD & Baran, PS 2016, 'Organic chemistry: A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents', Science, vol. 352, no. 6287, pp. 801-805. https://doi.org/10.1126/science.aaf6123
Qin, Tian ; Cornella, Josep ; Li, Chao ; Malins, Lara R. ; Edwards, Jacob T. ; Kawamura, Shuhei ; Maxwell, Brad D. ; Eastgate, Martin D. ; Baran, Phil S. / Organic chemistry : A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents. In: Science. 2016 ; Vol. 352, No. 6287. pp. 801-805.
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