Nickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols Enabled by Bidentate N-Heterocyclic Carbene (NHC)/Phosphine Ligands
Nazari, S. Hadi; Bourdeau, Jefferson E.; Talley, Michael R.; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; Michaelis, David J.; ACS Catalysis 8 (2017) 86–; doi:10.1021/acscatal.7b03079

data_4514298
_publ_section_title
;
 Nickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols
 Enabled by Bidentate N-Heterocyclic Carbene (NHC)/Phosphine Ligands
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              86
_journal_paper_doi               10.1021/acscatal.7b03079
_journal_volume                  8
_journal_year                    2017
_chemical_formula_sum            'C34.67 H38.67 Cl0.67 N1.33 Ni0.67 P0.67'
_chemical_formula_weight         557.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 97.999(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1807(13)
_cell_length_b                   21.777(2)
_cell_length_c                   15.5892(17)
_cell_measurement_temperature    100(2)
_cell_volume                     4431.1(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.215
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.496
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         8182
_refine_ls_number_restraints     540
_refine_ls_restrained_S_all      1.813
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.1167
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2832
_refine_ls_wR_factor_ref         0.2925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6391
_reflns_number_total             8182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03079_si_002.cif
_cod_data_source_block           17006
_cod_depositor_comments          'Adding full bibliography for 4514298.cif.'
_cod_database_code               4514298
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.505
_shelx_estimated_absorpt_t_max   0.715
_shelx_res_checksum              15228
_shelx_hkl_checksum              67275