@article {CHEM:CHEM201504959,
	title = {Exploring Regioselective Bond Cleavage and Cross-Coupling Reactions using a Low-Valent Nickel Complex},
	journal = {Chemistry {\textendash} A European Journal},
	volume = {22},
	number = {12},
	year = {2016},
	pages = {4070{\textendash}4077},
	abstract = {Recently, esters have received much attention as transmetalation partners for cross-coupling reactions. Herein, we report a systematic study of the reactivity of a series of esters and thioesters with [{(dtbpe)Ni}2(μ-η2:η2-C6H6)] (dtbpe=1,2-bis(di-tert-butyl)phosphinoethane), which is a source of (dtbpe)nickel(0). Trifluoromethylthioesters were found to form η2-carbonyl complexes. In contrast, acetylthioesters underwent rapid Cacyl-S bond cleavage followed by decarbonylation to generate methylnickel complexes. This decarbonylation could be pushed backwards by the addition of CO, allowing for regeneration of the thioester. Most of the thioester complexes were found to undergo stoichiometric cross-coupling with phenylboronic acid to yield sulfides. While ethyl trifluoroacetate was also found to form an η2-carbonyl complex, phenyl esters were found to predominantly undergo Caryl-O bond cleavage to yield arylnickel complexes. These could also undergo transmetalation to yield biaryls. Attempts to render the reactions catalytic were hindered by ligand scrambling to yield nickel bis(acetate) complexes, the formation of which was supported by independent syntheses. Finally, 2-naphthyl acetate was also found to undergo clean Caryl-O bond cleavage, and although stoichiometric cross-coupling with phenylboronic acid proceeded with good yield, catalytic turnover has so far proven elusive.},
	keywords = {CROSS-COUPLING, ELIMINATION, NICKEL, P ligands, SULFUR},
	issn = {1521-3765},
	doi = {10.1002/chem.201504959},
	url = {http://dx.doi.org/10.1002/chem.201504959},
	author = {Desnoyer, Addison N. and Friese, Florian W. and Chiu, Weiling and Drover, Marcus W. and Patrick, Brian O. and Love, Jennifer A.}
}
@inbook {25642,
	title = {Activation and Formation of Aromatic C{\textendash}F Bonds},
	booktitle = {Organometallic Fluorine Chemistry},
	series = {Topics in Organometallic Chemistry},
	volume = {52},
	year = {2015},
	pages = {55-111},
	publisher = {Springer International Publishing},
	organization = {Springer International Publishing},
	keywords = {CATALYSIS, CROSS-COUPLING, C{\textendash}F activation, C{\textendash}F bond formation, transition metals},
	isbn = {978-3-319-22095-6},
	doi = {10.1007/3418_2015_90},
	url = {http://dx.doi.org/10.1007/3418_2015_90},
	author = {LaBerge, NicoleA. and Love, JenniferA.},
	editor = {Braun, Thomas and Hughes, Russell P.}
}
@article {1109,
	title = {An asymmetric formal synthesis of fasicularin},
	journal = {Chemistry-a European Journal},
	volume = {11},
	number = {2},
	year = {2005},
	note = {ISI Document Delivery No.: 887VLTimes Cited: 20Cited Reference Count: 138},
	month = {Jan},
	pages = {639-649},
	type = {Review},
	abstract = {An asymmetric formal synthesis of fasicularin (1) is described. This natural product, isolated from the extracts of the marine invertebrate Nephteis fasicularis, has shown modest cytotoxicity towards Vero cells. Fasicularin is among only two members of the cylindricine family of natural products, along with lepadiformine (2), to possess a trans A-B ring junction. Key steps of this approach to 1 involve a siloxy-epoxide semipinacol rearrangement of 5 to 6, a B-alkyl Suzuki-Miyaura coupling reaction by using enol trifluoromethanesulfonate 19 and a substrate-directed hydrogenation reaction of 24. This formal synthesis also highlights the difficulty in the incorporation of the thiocyanate functionality present in 1.},
	keywords = {ALKALOIDS, ALPHA-HYDROXY EPOXIDES, ASCIDIAN CLAVELINA-CYLINDRICA, BETA-SILOXY ALDEHYDES, CROSS-COUPLING, CROSS-COUPLING REACTION, DIELS-ALDER REACTION, ENANTIOSPECIFIC, EPOXY SILYL ETHERS, MARINE ALKALOID LEPADIFORMINE, REGIOSELECTIVE OLEFIN INSERTION, ring expansion, SEMI-PINACOL REARRANGEMENT, semipinacol rearrangement, spirocycle},
	isbn = {0947-6539},
	url = {<Go to ISI>://000226333500017},
	author = {Fenster, M. D. B. and Dake, G. R.}
}
@article {830,
	title = {Synthesis of functionalized 1-azaspirocyclic cyclopentanones using Bronsted acid or N-bromosuccinimide promoted ring expansions},
	journal = {Journal of Organic Chemistry},
	volume = {69},
	number = {17},
	year = {2004},
	note = {ISI Document Delivery No.: 845XHTimes Cited: 19Cited Reference Count: 128},
	month = {Aug},
	pages = {5668-5675},
	type = {Review},
	abstract = {Azaspirocyclic ring systems are present in a variety of alkaloids. Functionalized 1-azaspirocyclopentanones (6, 7, 11, 12) can be efficiently constructed through semipinacol ring expansion reactions of 2-(1-hydroxycyclobutyl)-p-toluenesulfonylenamides (4) promoted by either a Bronsted acid ((S)-(+)-10-camphorsulfonic acid or HCI) or N-bromosuccinimide, an electrophilic bromine source. Reactions promoted by N-bromosuccinimide tend to proceed in higher yields (80-95\%) and with greater diastereoselectivity (3:1-1:0) compared to those reactions promoted by a Bronsted acid. In addition, N-bromosuccinimide promoted reactions can produce a complementary stereochemical outcome compared to the reactions using Bronsted acid.},
	keywords = {1ST TOTAL-SYNTHESIS, ALPHA-HYDROXY IMINES, AMINO KETONE REARRANGEMENTS, CROSS-COUPLING, DIELS-ALDER REACTION, ENANTIOSELECTIVE, INITIATED PINACOL REARRANGEMENT, MARINE ALKALOIDS, PINNAIC ACID, REACTIONS, THERMAL REARRANGEMENT, TOTAL-SYNTHESIS},
	isbn = {0022-3263},
	url = {<Go to ISI>://000223278200020},
	author = {Dake, G. R. and Fenster, M. D. B. and Hurley, P. B. and Patrick, B. O.}
}
@article {612,
	title = {A formal construction of fasicularin},
	journal = {Organic Letters},
	volume = {5},
	number = {23},
	year = {2003},
	note = {ISI Document Delivery No.: 741QDTimes Cited: 23Cited Reference Count: 42},
	month = {Nov},
	pages = {4313-4316},
	type = {Article},
	abstract = {Our synthetic approach toward fasicularin is presented. Key steps in this construction are a siloxy-epoxide semipinacol rearrangement, a B-alkyl Suzuki reaction and an intramolecular S(N)2 reaction.},
	keywords = {(+/-)-LEPADIFORMINE, CROSS-COUPLING, CYLINDRICINE, DIELS-ALDER REACTION, DIPOLAR CYCLOADDITION, ENANTIOMER, KETONES, MARINE ALKALOID LEPADIFORMINE, NATURAL, reaction, REARRANGEMENT, STEREOSELECTIVE CONSTRUCTION},
	isbn = {1523-7060},
	url = {<Go to ISI>://000186468000019},
	author = {Fenster, M. D. B. and Dake, G. R.}
}
@article {4929,
	title = {Regioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin},
	journal = {Journal of Porphyrins and Phthalocyanines},
	volume = {4},
	number = {3},
	year = {2000},
	note = {ISI Document Delivery No.: 302BXTimes Cited: 53Cited Reference Count: 13},
	month = {Apr-May},
	pages = {228-232},
	type = {Article},
	abstract = {5,15-Diphenylporphyrin was regiospecifically halogenated in high yield to give 5-iodo-15-bromo-10.20-diphenylporphyrin, which was then subjected to Heck and Stille-type coupling reactions to form unsymmetrically substituted porphyrins. The regioselectivity of the iodination of diphenylporphyrins and subsequent formation of amphiphilic porphyrins via palladium-based methodology was also studied. The utility of this method for the synthesis of photodynamic sensitisers has been demonstrated on AR4-2J rat pancreatic carcinoma cells. Copyright (C) 2000 John Wiley \& Sons, Ltd.},
	keywords = {ALKYNYLATION, amphiphiles, CROSS-COUPLING, IODINATION, palladium, PHOTODYNAMIC THERAPY, porphyrins},
	isbn = {1088-4246},
	url = {<Go to ISI>://000086346000002},
	author = {Shanmugathasan, S. and Johnson, C. K. and Edwards, C. and Matthews, E. K. and Dolphin, D. and Boyle, R. W.}
}
