Nickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions
Shaozhong Ge; John F. Hartwig; Journal of the American Chemical Society 133 (2011) 16330–16333; doi:10.1021/ja2082087

data_4106976
_publ_section_title
;
 Nickel-Catalyzed Asymmetric \a-Arylation and Heteroarylation of Ketones
 with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and
 Room-Temperature Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16330
_journal_page_last               16333
_journal_paper_doi               10.1021/ja2082087
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C51 H37 N Ni P2, C7 H8 '
_chemical_formula_sum            'C58 H45 N Ni P2'
_chemical_formula_weight         876.60
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.857(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.764(3)
_cell_length_b                   11.550(3)
_cell_length_c                   17.936(4)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.28
_cell_volume                     2224.8(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2010.11-3 (Bruker, 2010)'
_computing_data_reduction
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  Compound4
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24908
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.8555
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             916
_exptl_crystal_id                Compound4
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research)  with the (2 3 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack (1983),  4020 Friedels'
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         8520
_refine_ls_number_restraints     445
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                7919
_reflns_number_total             8520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2082087_si_002.cif
_cod_data_source_block           Compound4
_cod_original_cell_volume        2225.0(9)
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4106976