title: Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.
abstract: Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Tian
authors.initials: T
authors.lastname: Qin
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Lara R
authors.initials: LR
authors.lastname: Malins
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Jacob T
authors.initials: JT
authors.lastname: Edwards
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Rohan R
authors.initials: RR
authors.lastname: Merchant
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Alexander J E
authors.initials: AJ
authors.lastname: Novak
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Jacob Z
authors.initials: JZ
authors.lastname: Zhong
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Riley B
authors.initials: RB
authors.lastname: Mills
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Yan
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, NJ, 08903, USA.
authors.forename: Changxia
authors.initials: C
authors.lastname: Yuan
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, NJ, 08903, USA.
authors.forename: Martin D
authors.initials: MD
authors.lastname: Eastgate
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Phil S
authors.identifier: 0000-0001-9193-9053
authors.initials: PS
authors.lastname: Baran
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D004583:Electrons; D004952:Esters / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D004952:Esters; D005609:Free Radicals; D010797:Phthalimides; D009532:Nickel; C037437:N-hydroxyphthalimide
keywords: conjugate addition; decarboxylation; esters; nickel catalysis; redox-active