Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 25, Pages 8887-8890Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja503909c
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Funding
- NIH [R01 GM084254]
- NSF [CHE-1301343]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1301343] Funding Source: National Science Foundation
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By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3' position, the derived gold(I) complex possesses orthogonally positioned push and pull forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pK(a) units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.
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