Alkynes as Allylmetal Equivalents in Redox-Triggered C–C Couplings to Primary Alcohols: (Z)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C–H Oxidative Addition | Zendy

Boyoung Y. Park | Zendy; Khoa D. Nguyen | Zendy; Mani Raj Chaulagain | Zendy; Venukrishnan Komanduri | Zendy; Michael J. Krische | Zendy

Open Access

Alkynes as Allylmetal Equivalents in Redox-Triggered C–C Couplings to Primary Alcohols: (Z)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C–H Oxidative Addition

Author(s) -

Boyoung Y. Park,

Khoa D. Nguyen,

Mani Raj Chaulagain,

Venukrishnan Komanduri,

Michael J. Krische

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja505962w

Subject(s) - chemistry , propargyl , ruthenium , catalysis , primary (astronomy) , redox , propargyl alcohol , oxidative phosphorylation , alcohol oxidation , medicinal chemistry , organic chemistry , physics , astronomy , biochemistry

The cationic ruthenium catalyst generated upon the acid-base reaction of H2Ru(CO)(PPh3)3 and 2,4,6-(2-Pr)3PhSO3H promotes the redox-triggered C-C coupling of 2-alkynes and primary alcohols to form (Z)-homoallylic alcohols with good to complete control of olefin geometry. Deuterium labeling studies, which reveal roughly equal isotopic compositions at the allylic and distal vinylic positions, along with other data, corroborate a catalytic mechanism involving ruthenium(0)-mediated allene-aldehyde oxidative coupling to form a transient oxaruthenacycle, an event that ultimately defines (Z)-olefin stereochemistry.

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