Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides
Soumik Biswas; Daniel J. Weix; Journal of the American Chemical Society 135 (2013) 16192–16197; doi:10.1021/ja407589e

data_4121026
_publ_section_title
;
 Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling
 of Aryl Halides with Alkyl Halides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16192
_journal_page_last               16197
_journal_paper_doi               10.1021/ja407589e
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C18 H24 I2 N2 Ni'
_chemical_formula_sum            'C18 H24 I2 N2 Ni'
_chemical_formula_weight         580.90
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_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
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_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
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_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0707
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_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
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_diffrn_reflns_limit_k_min       -21
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        33.730
_diffrn_reflns_theta_max         33.766
_diffrn_reflns_theta_min         2.452
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.861
_exptl_absorpt_correction_T_max  0.7467
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_exptl_crystal_size_mid          0.18
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_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+2.4840P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja407589e_si_002.cif
_cod_data_source_block           weixsb03
_cod_database_code               4121026
_shelx_estimated_absorpt_t_min   0.543
_shelx_estimated_absorpt_t_max   0.748
_shelxl_version_number           2013-2
_shelx_res_checksum              87837